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

HRID 1643946Notes

Reaction equation

HRID 1643946 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9](=[O:22])[N:8]([CH:23]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:24]([O:26]C(C)(C)C)=[O:25])[C:7]=2[CH:37]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)(=[O:13])=[O:12])[C:9](=[O:22])[N:8]([CH:23]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:24]([OH:26])=[O:25])[C:7]=2[CH:37]=1)#[N:2]

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-4526b7ce14394862aeee01b3ed0186f1
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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