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

HRID 1631963Notes

Reaction equation

HRID 1631963 reaction equation
C([O:5][C:6](=[O:37])[CH:7]([N:14]1[C:18]2[CH:19]=[C:20]([C:23]#[N:24])[CH:21]=[CH:22][C:17]=2[N:16]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:15]1=[O:36])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:23]([C:20]1[CH:21]=[CH:22][C:17]2[N:16]([S:25]([C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)(=[O:27])=[O:26])[C:15](=[O:36])[N:14]([CH:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:6]([OH:37])=[O:5])[C:18]=2[CH:19]=1)#[N:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642498HCID 86642498, compound

Product 1

HCID 24900959[6-Cyano-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]phenylacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.75 g (3.37 mmol) of tert-butyl[6-cyano-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]phenylacetate (XIIc) were dissolved in dichloromethane (20 ml) and, while stirring at room temperature, trifluoroacetic acid (10 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: 1.49 g (96%) 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-6848dbbdfc7345619862c86e84a68ec0
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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