Tag: M.W=200-300

Synthetic Route of 89459-38-1, These common heterocyclic compound, 89459-38-1, name is 2-Iodo-4-nitrobenzoic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of Example 2.140.1 (130 g) in a mixture of methanol (1000 mL) and sulfuric acid (23.65 mL) was stirred at 85 C for 16 hours and concentrated to dryness. The residue was triturated with methanol (100 mL) and the suspension was stirred for 10 minutes. The solid was collected by filtration, washed with water (200 mL x 3) and methanol (20 mL), and air-dried for 16 hours to give the title compound. MS (LC-MS) m/e 308.0 (M+H)+.

The synthetic route of 89459-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (808 pag.)WO2017/214462; (2017); A2;,
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Application of 40400-15-5, A common heterocyclic compound, 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, molecular formula is C8H6IN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

30.0 g (0.123 mol) of 2-iodophenylacetonitrile, 66.0 g (0.370 mol) of diphenylacetylene, 11.3 g (0.0123 mol) of tris(dibenzylideneacetone)dipalladium, 30.0 g (0.123 mol) of triethylamine, 210 mL of dimethylformamide, and 30 mL of water were stirred in a round-bottom flask at 130 C. for 48 h. After completion of the reaction, the organic layer was extracted, purified by column chromatography, and dried to afford 28 g of Intermediate 11-a (yield 77%).

The synthetic route of 40400-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC CO., LTD.; LEE, Se-jin; LEE, Bong-Hyang; YU, Taejung; CHOI, Yeongtae; LEE, Dajung; (58 pag.)US2019/140177; (2019); A1;,
Iodide – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 75581-11-2 as follows. Product Details of 75581-11-2

Tri(o-tolyl)phosphine (30 mg, 0.1 mmol) and palladium (II) acetate (11.0 mg, 0.05 mmol) were dissolved in hexamethylphosphoramide (0.1 mL). The mixture was stirred for 5 min, then water (0.9 mL), potassium carbonate (0.42 g, 3 mmol), acrylic acid (1.14 mL, 2 mmol) and 4-iodo-1-methoxy-2-methylbenzene S1 (0.25 g, 1 mmol) obtained above were added. The mixture was stirred at 90 C for 5 h, filtered and the solution was acidified with conc. H2SO4 (to pH 1). The milky suspension was extracted with ethyl acetate (30 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent evaporated. The resulting solid was recrystallized from isopropanol to give 12b as a pale yellow solid (0.115g, 60 %); mp 200-201 C, (lit. 201 C) identical (1H NMR) to that described.

According to the analysis of related databases, 75581-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Martinez, Mario David; Riva, Diego Ariel; Garcia, Cybele; Duran, Fernando Javier; Burton, Gerardo; Molecules; vol. 25; 4; (2020);,
Iodide – Wikipedia,
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Some common heterocyclic compound, 19230-50-3, name is 2-Iodo-5-nitrobenzoic acid, molecular formula is C7H4INO4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C7H4INO4

I. 2-Iodo-5-Nitro-Benzamide 2-iodo-5-nitro-benzamide was synthesised by the method previously described for 4-iodo-5-nitro-benzamide using 2-iodo-5-nitro benzoic acid (Chemica Alta Ltd., Edmonton, Alberta, Canada) as the starting material. 1 H NMR Spectrum, in DMSO-d6 delta (ppm) values relative to TMS: 7.742 (1H, singlet); 7.943 (1H, doublet of doublts, J=8.26 Hz, J=2.58 Hz); 8.034 (1H, singlet), 8.064 (1H, doublet, J=2.94 Hz); and 8.191 (1H, doublet, J=8.46 Hz). Mass Spectrum: Low resolution electron impact spectrum (m/z): 292 (M+), 276, 230, 202, 165, 127, 91, 75, 63. High resolution measurement of M+: Calculated for C7 H5 IN2 O3: 291.934494; found: 291.934149 (deviation=1.2 ppm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19230-50-3, its application will become more common.

Reference:
Patent; Octamer, Inc.; US5877185; (1999); A;,
Iodide – Wikipedia,
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Reference of 5876-51-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5876-51-7 as follows.

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl2 (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na2CO3 (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N2 and stirred at 110 C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH3OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4, concentrated and purified on silica using EtOAc/Heptane 1:20 ? 1:9 step gradient) to afford 2′-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

According to the analysis of related databases, 5876-51-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Saleeb, Michael; Mojica, Sergio; Eriksson, Anna U.; Andersson, C. David; Gylfe, Asa; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1077 – 1089;,
Iodide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Fluoro-6-iodobenzoic acid

Method B: 2-Fluoro-6-[1 ,2,3]triazol-2-yl-benzoic acid. To a 2 L, 3- necked, round-bottomed flask equipped with an overhead mechanical stirrer, thermocouple probe, heating mantle, reflux condenser, and nitrogen inlet were added 2-fluoro-6-iodobenzoic acid (127.6 g, 480 mmol), copper iodide (4.57 g, 24 mmol), and Cs2C03 (312.6 g, 959 mmol). To these solids were added dioxane (640 mL), then water (2.6 mL, 144 mmol), then 1 H-1 ,2,3-triazole (55.6 mL, 959 mmol), and finally frans-1 ,2-dimethylcyclohexane-1 ,2-diamine (15.1 mL, 96 mmol). The mixture was then warmed to 60 C for 30 min, then to 83 C for 30 min, and then to 100 C for 3 h. After the 3 h at 100 C, the mixture was cooled and then 1 L of MTBE and 1 L of water were added. After vigorous mixing, the layers were separated and the bottom aqueous layer was acidified to pH 1 .72 with -148 mL of concentrated hydrochloric acid. The aqueous was then extracted twice with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated to provide a dark oil. The oil was stirred overnight in EtOAc (450 mL) and the resulting precipitate was removed by filtration. The mother-liquors were concentrated to a brown solid (106.21 g, 75 wt% by quantitative HPLC, 79.7 g, 80%). 1H NMR (400 MHz, DMSO-d6): 8.22 – 8.13 (bs, 2H), 7.84-7.80 (m, 1 H), 7.74 – 7.65 (m, 1 H), 7.50 – 7.41 (m, 1 H).

According to the analysis of related databases, 111771-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 645-00-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 645-00-1 name is 1-Iodo-3-nitrobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Iodo-3-nitrobenzene, and friends who are interested can also refer to it.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
Iodide – Wikipedia,
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Electric Literature of 6414-69-3, The chemical industry reduces the impact on the environment during synthesis 6414-69-3, name is Ethyl 3-iodopropanoate, I believe this compound will play a more active role in future production and life.

Ethyl 3-[4-(3-Nonynyloxymethyl) phenyl]propanoate (46). A flask was charged with Zn-Cu couple (200 mg, 3 mmol) solution of ethyl 3-iodopropanoate (510 mg, 2 mmol) in dry toluene (4 mL) and dry N,N-dimethylacetamide (2mL) was added. The mixture was vigorously stirred for 1 hour at room temperature and then heated at gentle reflux for 4.5 hours. After the mixture was cooled to 60 C, a solution of tetrakis(triphenylphosphine)palladium(0)(30 mg, 0.026 mmol) in toluene (2 mL) was added over 1 minute and stirring was continued for 5 minutes at the same temperature. A solution of (45) (309 mg, 1 mmol) in dry toluene (2 mL) was added and the mixture was refluxed for 12 hours. The reaction mixture was allowed to cool to 25 C. and filtered through a Celite pad. The filter cake was washed with ether (50 mL). The filtrate was successively washed with a solution of i N ammonium chloride (10 mL), a solution of saturated sodium hydrogen carbonate (10 mL) and a solution of saturated sodium chloride (10 mL). The aqueous phases were back extracted with ether (30 mL), the combined organic extracts were dried (MgSO4), filtered, concentrated by rotary evaporation to yield a yellow oil. Purification by flash silica gel chromatography (97:03 petroleum ether/EtOAc) afforded (46) (165 mg, 51%) as a colorless oil: Rf 0.44 (95:05 petroleum ether/EtOAc); 1 H NMR (CDCl3) delta 7.19 (m, 4 H), 4.51 (s, 2 H), 4.12 (q, J=7.2 Hz, 2 H), 3.55 (t, J=7.2 Hz, 2 H), 2.94 (t, J=8.1 Hz, 2 H), 2.61 (t, J=8.1 Hz, 2 H), 2.46 (tt, J1 =6.9 Hz, J2 =2.1 Hz, 2 H), 2.13 (tt, J1 =7.2 Hz, J2 =2.4 Hz, 2 H), 1.40 (m, 6 H), 1.22 (t, J=7.2 Hz, 3 H), 0.88 (t, J=6.9 Hz, 3 H); 13 C NMR (CDCl3) delta 173.01, 140.87, 138.58, 128.68, 127.75, 81.64, 76.67, 72.99, 69.15, 60.53, 36.02, 31.01, 31.18, 28.81, 22.34, 20.28, 18.85, 14.32, 14.12. STR14

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 3-iodopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Board of Governors of Wayne State University; Vanderbilt University; US5238832; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 124700-41-0 as follows. COA of Formula: C7H4FIO2

General procedure: A mixture of various carboxylic acids (1.0mmol), an excess of thionyl chrolide (5mL) was refluxed for 2h and concentrated in vacuo to give corresponding acyl chloride (quant).

According to the analysis of related databases, 124700-41-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Yin-Bo; Li, Ji-Ling; Shao, Xu-Sheng; Xu, Xiao-Yong; Li, Zhong; Chinese Chemical Letters; vol. 24; 8; (2013); p. 673 – 676;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 696-41-3,Some common heterocyclic compound, 696-41-3, name is 3-Iodobenzaldehyde, molecular formula is C7H5IO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

14.4: (3-iodo-benzyl)-dimethyl-amine To a cold (0C) solution of 3-iodo-benzaldehyde (3g, 12.9 mmol) in anhydrous dichloromethane (130 ml) were added acetic acid (1.9ml) and N,N-dimethylacetamide. The yellow solution is stirred 10 minutes at 0C and sodium triacetoxyborohydride (6.85g, 32.33 mmoles) is added by portions. The resulting mixture is stirred at room temperature for 90 minutes and evaporated to dryness under reduced pressure. Ethyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue and the two layers were separated The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to yield (3-iodo-benzyl)-dimethyl-amine (3.05g, 90%) as a brown oil. LC/MS (Method LC8): Rt = 0.86 min; m/z = 262 [M+H]+.

The synthetic route of 696-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; Loehn, Matthias, Dr.; Mendez-Perez, Maria, Dr.; Pfeiffer-Marek, Stefania, Dr.; Kannt, Aimo, Dr.; Begis, Guillaume, Dr.; Jeannot, Frederic, Dr.; Duclos, Olivier; EP2567959; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com