Trifluoroacetic acid → HCID 23290190, compound

HRID 366853Notes

Reaction equation

HRID 366853 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[C:13]4[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][C:16]([OH:18])=[O:17])[C:13]4[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23290175HCID 23290175, compound2×

Product 1

HCID 23290190HCID 23290190, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 0.5 g (1.42 mmol) of 1,1-dimethylethyl 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-acetate (the title compound of EXAMPLE 2) in 10 mL of chloroform was treated with 10 mL of trifluoro-acetic acid (TFA), and the reaction was stirred at rt until completion. Volatiles were evaporated in vacuo, and the residue was recrystallized from ether to give 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-acetic acid as a white solid: 1H NMR (DMSO, d6) δ 5.25 (s, 2H), 6.18 (s, 2H), 7.19 (d, J=8.1 Hz, 1H), 7.23-7.35 (m, 2H), 7.37-7.53 (m, 2H), 7.70-7.87 (m, 2H); HRMS (EI) Calc'd for M+ : 297.0875, found: 297.0885. Anal. Calc'd for [C16H12N2O4 +0.67 CF3CO2H]: C, 55.91; H, 3.43; N, 7.52. Found: C, 55.91; H, 3.52; N, 7.51.

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-a6c3939d9e4c4f9c9e6aa3531b75aac3
Source dataset
uspto-grants-2000_10
Patent number
US06130333

Reaction notes

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