Hydrochloric Acid → 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide
Reaction equation
CO[C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:8]2[N:9]=CNC=2[CH:6]=1)=[O:4].[CH3:24][O:25]C(C1C(NC2C=CC(Br)=CC=2)=C(Cl)C2N=CNC=2C=1)=O.C1C(=O)[N:50](Cl)C(=O)C1.Cl.[C:55](=[O:58])(O)[O-].[Na+].OS([O-])=O.[Na+].[CH3:65][N:66]([CH:68]=O)[CH3:67]>O>[OH:25][CH2:24][CH2:55][O:58][NH:50][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:8]2[N:9]=[CH:68][N:66]([CH3:65])[C:67]=2[CH:6]=1)=[O:4]Participants
9
Reactant 7
HCID 313Hydrochloric Acid
HCID 6228Dimethylformamide
HCID 31398Chlorosuccinimide2×
HCID 516892Sodium Bicarbonate
HCID 23665763Sodium Bisulfite
HCID 668983426-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester
HCID 688177756-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl esterProduct 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- additionis added
- filtrationSolids are filtered
- washwashed with water and ether
Sources & evidence
- ORD record
- ord-f22dfc2f60fe43d6a94f5097c8ccc3d5
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193230B2
Reaction notes
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