Tag: M.W=200-300

Some common heterocyclic compound, 74534-15-9, name is 1-Chloro-2-iodo-4-nitrobenzene, molecular formula is C6H3ClINO2, 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. Recommanded Product: 74534-15-9

A mixture of compound 2 (10 mmol), iron powder (30 mmol) and saturated NH4Cl aqueous (10 mL) in EtOH (40 mL) was stirred at 75 C for 3 h. The reaction mixture was filtered through celite and the residue was washed with CH2Cl2. The filtrate was evaporated to remove most of EtOH, and then dissolved in CH2Cl2. The organic mixture was washed with water and brine, dried over Na2SO4, and condensed to give a yellow solid, yield 97%. 1H NMR (400 MHz, DMSO-d6) delta 7.14 (dd, J = 5.6, 3.0 Hz, 2H), 6.58 (dd, J = 8.6, 2.7 Hz, 1H), 5.42 (s, 2H). 13C NMR (101 MHz, DMSO) delta 149.28, 129.58, 124.68, 123.10, 115.86, 98.96.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74534-15-9, its application will become more common.

Reference:
Article; Li, Wenlu; Sun, Qinsheng; Song, Lu; Gao, Chunmei; Liu, Feng; Chen, Yuzong; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 721 – 733;,
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,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

Related Products of 146137-72-6,Some common heterocyclic compound, 146137-72-6, name is 2-Fluoro-6-iodobenzaldehyde, molecular formula is C7H4FIO, 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.

General procedure: The crude starting material (10) was dissolved in DMSO (25 mL) and methyl thioglycolate (2.6 mL, 1.1 equiv.) was added dropwise under Ar at RT. Triethylamine (7.45 mL, 2.2 equiv.) was then added and the mixture was heated at 70 C for 5 hours. The reaction mixture was cooled to RT and poured slowly into vigorously stirred ice-water (250 mL). After 30 min of stirring, a light yellow precipitate was collected by filtration, rinsed with H2O, and dried in vacuo to afford a crude yellow solid (6.40 g, 80% crude yield). The product was used for the next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-6-iodobenzaldehyde, its application will become more common.

Reference:
Article; Hur, Wooyoung; Rosen, Hugh; Gray, Nathanael S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 1 – 5;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 51628-12-7, The chemical industry reduces the impact on the environment during synthesis 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, I believe this compound will play a more active role in future production and life.

To a stirred solution of 2-(4-iodophenyl)acetonitrile (10 g, 41 .15 mmol) in tetrahydrofuran (100 ml) was added drop wise lithium bis(trimethylsilyl)amide (103 ml of a 1 M solution in tetrahydrofuran, 103 mmol) at -78 C. The resulting mixture was allowed to stirre for 15 minutes. The 3-(chloromethyl)pyridine hydrochloride (6.75 g, 41.15 mmol) was then added. The reaction was then allowed to react overnight at room temperature. The reaction was monitored by thin layer chromatography and showed completion after one night of stirring. Water (100 ml) and ethyl acetate (100 ml) were added. The organic phase was isolated and concentrated under reduced pressure The crude product was then absorbed onto silica gel and purified by flash chromatography to give 4.7 g of 2-(4-iodophenyl)-3-(3- pyridyl)propanenitrile

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, 2-(4-Iodophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JEANMART, Stephane Andre Marie; RAJAN, Ramya; BONVALOT, Damien; PERRUCCIO, Francesca; WO2015/14733; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 335349-57-0,Some common heterocyclic compound, 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, molecular formula is C6H4ClIN2O2, 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.

Example E1 5-Allyloxy-4-iodo-2-nitro-phenylamine Prepared from 5-chloro-4-iodo-2-nitro-phenylamine (Example Al) (15.0 g, 50 mmol), allyl alcohol (50 mL) and KOH (7.96 g, 121 mmol) in DMSO (50 mL) according to the general procedure E. Obtained as an orange solid (9.38 g). MS (EI) 320 (M+); mp 74 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-4-iodo-2-nitroaniline, its application will become more common.

Reference:
Patent; Hoffmann-la Roche Inc.; US6407094; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 13421-00-6, 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 13421-00-6 as follows.

EXAMPLE 64a Preparation of intermediate 5-chloro-2-Iodo-benzaldehyde To a solution of 5-chloro-2-iodo benzoic acid (4.92 g, 17 mmol) (TRANS) in anhydrous tetrahydrofuran (100 mL) at 0 C. was added borane tetrahydrofuran (1 M, 34 mL, 34 mmol) dropwise. The reaction mixture was then stirred at room temperature for 18 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give a colorless oil. The oil was dissolved into 1,2-dichloroethane (50 mL), and activated MnO2 (15 g) was added. The mixture was then heated at reflux for 2 h, cooled to room temperature, and filtered through a short pad of celite. The filtrated was concentrated and purified by chromatography (EtOAc:hexanes=1;8) to give 5-chloro-2-Iodo-benzaldehyde as a white solid (Yield 5.5 g, 25%).

According to the analysis of related databases, 13421-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 6828-35-9, name is 5-Chloro-2-iodoaniline, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6828-35-9, category: iodides-buliding-blocks

In a round bottom flask, 5-chloro-2-iodoaniline (2.00 g, 7.89 mmol), methyl propargylether (1.00 mL, 11.84 mmol) and TEA (1.92 mL, 13.41 mmol) were diluted in DMF.The mixture was degassed (N2 bubbling) and Pd(PPh3)2C12 (0.28 g, 0.39 mmol) andCul (0.30 g, 1.58 mmol) were added. The reaction mixture was stirred at rt for 4 h.Thereaction mixture was aprtitionned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude was purified by column chromatography on silica gel (irregular Si02, 40 g, mobile phase:heptane/EtOAc, gradient from 90:10 to 80:20). The product fractions were concentrated to afford 1.0 13 g of intermediate 376 (70% yield, orange liquid which solidify upon standing).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com