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

HRID 2104072Notes

Reaction equation

HRID 2104072 reaction equation
C[O:2][C:3]([C:5]1[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[Cl:23])=[C:13]([Cl:24])[C:8]2[N:9]=[CH:10][N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].C1COCC1.O.[OH-].[Na+].Cl>O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:14]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]3[N:11]([CH3:12])[CH:10]=[N:9][C:8]=3[C:13]=2[Cl:24])=[C:17]([Cl:23])[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21881883Oxolane--water (1/1)HCID 688173586-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 211142006-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester 10ee (21 mg, 0.048 mmol) is dissolved into 2:1 THF/water (1.2 mL) and NaOH (0.190 mL, 1.0 M aqueous solution, 0.190 mmol) is added. After stirring for 4 hours the reaction is diluted with water and acidified to pH 2 by addition of 1.0 M HCl. The mixture is then extracted with 3:1 EtOAc/THF (3×), dried (Na2SO4) and concentrated to give quantitative yield of desired product as a white solid. MS APCI (+) m/z 414, 416 (M+, Br pattern) detected.

Workup

  1. additionis added
  2. extractionThe mixture is then extracted with 3:1 EtOAc/THF (3×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a92a6a635944b218e895eedb7f0761e
Source dataset
uspto-grants-2009_08
Patent number
US07576114B2

Reaction notes

Loading…