HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium Bisulfite | HCID 23665763 | — |
| Reactant | 6-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester | HCID 66898342 | — |
| Reactant | 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester | HCID 68817775 | — |
| Solvent | Water | HCID 962 | — |
| Product | 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide | HCID 58890625 | 57% |
Reaction Steps
6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester 10dd: 6-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester 8g (0.225 g, 0.591 mmol) is dissolved in DMF (2 mL) and NCS (79 mg, 0.591 mmol) is added. After the NCS is in solution concentrated HCl (0.005 mL, 0.059 mmol) is added. After 2 hours, sodium bicarbonate, water and NaHSO3 are added to the reaction mixture. Solids are filtered and washed with water and ether to give 0.141 g (57%) of clean desired product as a tan solid. MS APCI (−) m/z 414, 416 (M−, Br pattern) detected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08193231B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-f2ef374593604bbe82d04f779e7acbf0 |
| Source note | uspto-grants-2012_06 |