3,5-Dimethoxyaniline → 2-(1H-Benzimidazol-1-yl)-N-(3,5-dimethoxyphenyl)acetamide

HRID 1991221Notes

Reaction equation

HRID 1991221 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.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[NH2:26]>>[N:12]1([CH2:11][C:8]([NH:26][C:25]2[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:23]([O:22][CH3:21])[CH:24]=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 663013,5-DimethoxyanilineHCID 1785258373-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate

Product 1

HCID 262178992-(1H-Benzimidazol-1-yl)-N-(3,5-dimethoxyphenyl)acetamide

Procedure

The title compound was synthesized according to a procedure described in Example 98 starting from 3-carboxymethyl-3H-benzoimidazol-1-ium trifluoro-acetate (Example 92 part B) and 3,5-dimethoxy-aniline. Calculated for C17H17N3O3 m/z: 311.34, found 311.88 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.69 (s, 6 H), 5.14 (s, 2H), 6.23 (t, J=2.3 Hz, 1H), 6.82 (d, J=2.0 Hz, 2H), 7.22 (m, 2H), 7.51 (d, J=7.6 Hz, 1H), 7.66 (dd, J=7.3, 1.3 Hz, 1H), 8.21 (s, 1H), 10.41 (s, 1H).

Sources & evidence

ORD record
ord-c16dce26eb564af9b81f1d9d880674e4
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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