Trifluoroacetic acid → 3-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate

HRID 1991212Notes

Reaction equation

HRID 1991212 reaction equation
C([O:5][C:6](=[O:17])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1)(C)(C)C.[F:18][C:19]([F:24])([F:23])[C:20]([O-:22])=[O:21].C(CN1C2C=CC=CC=2[NH+]=C1)(O)=O.FC(F)(F)C(O)=O>ClCCl>[F:18][C:19]([F:24])([F:23])[C:20]([O-:22])=[O:21].[C:6]([CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH+:10]=[CH:9]1)([OH:17])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451214HCID 178451214, compound

Product 1

HCID 1785258373-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part B: Synthesis of 3-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate tert-Butyl 1H-benzimidazol-1-ylacetate (110 mg, 0.47 mmol) was dissolved in dichloromethane (3 mL) and trifluoroacetic acid (1 mL) was added. The reaction was stirred at ambient temperature for 24 h and the solvents were removed to afford 3-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate (136 mg, 100%). Mass spectrum (ESI) m/z: 177.0. 1H NMR (400 MHz, CD3OD) δ ppm 5.3 (s, 2H), 7.5 (m, 2H), 7.8 (m, 2H), 9.4 (s, 1H).

Workup

  1. customthe solvents were removed

Sources & evidence

ORD record
ord-8b16de5263144b6a9fee0529cceec23e
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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