3-Fluoro-4-methylaniline → 2-(benzimidazol-1-yl)-N-(3-fluoro-4-methylphenyl)acetamide

HRID 1991214Notes

Reaction equation

HRID 1991214 reaction equation
FC(F)(F)C([O-])=O.[C:8]([CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH+:14]=[CH:13]1)([OH:10])=O.[F:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[CH3:29])[NH2:25]>>[N:12]1([CH2:11][C:8]([NH:25][C:24]2[CH:26]=[CH:27][C:28]([CH3:29])=[C:22]([F:21])[CH:23]=2)=[O:10])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Participants

3

Reactant 2

HCID 99573-Fluoro-4-methylanilineHCID 1785258373-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate

Product 1

HCID 64588252-(benzimidazol-1-yl)-N-(3-fluoro-4-methylphenyl)acetamide

Procedure

The title compound was synthesised according to the procedure described in Example 89, from 3-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate and 3-fluoro-4-methyl-aniline. Yield 12 mg (35%). Calculated for C16H14FN3O m/z: 283.3, found 284.3 [M+H]+. 1H NMR (400 MHz, CD3OD) δ ppm 2.2 (s, 3H), 5.1 (s, 2H), 7.1 (m, 2H), 7.3 (m, 2H), 7.4 (d, J=11.6 Hz, 1H), 7.5 (d, J=8.6 Hz, 1H), 7.7 (m, 1H), 8.1 (s, 1H).

Sources & evidence

ORD record
ord-261c24dad94f4d42ba14ab47e147f700
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

Loading…