5-Benzimidazolecarboxylic acid → HCID 178434981, compound

HRID 1983107Notes

Reaction equation

HRID 1983107 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:15][NH2:16])=[O:14].[N:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26](O)=O)=[CH:25][C:20]=2[NH:19][CH:18]=1>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:14][C:26]([C:24]2[CH:23]=[CH:22][C:21]3[NH:17][CH:18]=[N:19][C:20]=3[CH:25]=2)=[N:16][N:15]=1

Participants

3

Reactant 2

HCID 4594565-Benzimidazolecarboxylic acidHCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazide

Product 1

HCID 178434981HCID 178434981, compoundYield 5%

Procedure

As described for example 2, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (400 mg, 1.84 mmol) was converted using benzimidazole-5-carboxylic acid instead of o-toluic acid to the title compound (SiO2, heptane:ethyl acetate:dichloromethane:methanol=70:20:10:0 to 0:80:10:10, 33 mg, 5%) which was obtained as an off-white solid. MS: m/e=344.1 [M+H]+.

Sources & evidence

ORD record
ord-afcef99ef51642099e77b9ae4dbd5511
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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