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

HRID 1643934Notes

Reaction equation

HRID 1643934 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[C:8](=[O:21])[N:7]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[C:6]=2[CH:30]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([S:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)(=[O:12])=[O:11])[C:8](=[O:21])[N:7]([CH2:22][C:23]([OH:25])=[O:24])[C:6]=2[CH:30]=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-3a2ec9e2773c4442a1c9bc7c044df69f
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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