Trifluoroacetic acid → [6-Chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]acetic acid

HRID 1631951Notes

Reaction equation

HRID 1631951 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:9]1=[O:29])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]2[N:10]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[C:9](=[O:29])[N:8]([CH2:7][C:6]([OH:30])=[O:5])[C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642493Tert-butyl[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]acetate

Product 1

HCID 66755371[6-Chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.10 g (2.43 mmol) of tert-butyl[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]acetate (XIIg) were dissolved in dichloromethane (40 ml) and, while stirring at room temperature, trifluoroacetic acid (20 ml) was added. The reaction solution was stirred for 2 h and then the solvent and excess trifluoroacetic acid were removed in vacuo. The residue was taken up again in toluene, concentrated in vacuo and then dried in vacuo. Yield: 0.82 g (95%) of white solid

Workup

  1. stirringThe reaction solution was stirred for 2 h
  2. customthe solvent and excess trifluoroacetic acid were removed in vacuo
  3. concentrationconcentrated in vacuo
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b08a38db0df34c098aeda74dee391063
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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