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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1895489Generated: October 30, 2026

Hydrochloric Acid → 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide

https://huagongshe.com/reaction/1895489

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantDimethylformamideHCID 6228—
ReactantChlorosuccinimideHCID 31398—
ReactantSodium BicarbonateHCID 516892—
ReactantSodium BisulfiteHCID 23665763—
Reactant6-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl esterHCID 66898342—
Reactant6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl esterHCID 68817775—
SolventWaterHCID 962—
Product6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amideHCID 5889062557%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08513293B2
Source datasetuspto-grants-2013_08
ORD IDord-11f02f6e66274243a4ab05a771f60143
Source noteuspto-grants-2013_08