2,6-Dichloro-4-(trifluoromethyl)phenylacetic acid → 2-[2,6-Dichloro-4-(trifluoromethyl)benzyl]-1-methyl-1H-benzimidazol-7-amine

HRID 1665224Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH2:13][C:14](O)=O.[CH3:17][NH:18][C:19]1[C:24]([NH2:25])=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH2:13][C:14]1[N:18]([CH3:17])[C:19]2[C:24]([NH2:25])=[CH:23][CH:22]=[CH:21][C:20]=2[N:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of [2,6-dichloro-4-(trifluoromethyl)phenyl]acetic acid (273 mg, 1.00 mmol) in toluene (2.0 mL) was added N,N′-carbonyldiimidazole (162 mg, 1.00 mmol) at room temperature. After the reaction mixture was stirred at 50° C. for 15 min, N2-methylbenzene-1,2,3-triamine (137 mg, 1.00 mmol) in toluene (2 mL) was added to the mixture, and the mixture was refluxed for further 60 hr. After the reaction mixture was cooled, the solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography eluting with 40-60% ethyl acetate/n-hexane gradient mixture to give the title compound (170 mg, 0.455 mmol, 45%) as a colorless solid. The resulting solid was recrystallized from n-hexane/ethyl acetate to give the title compound (137 mg, 0.38 mmol).

Workup

temperaturethe mixture was refluxed for further 60 hr
temperatureAfter the reaction mixture was cooled
customthe solvent was evaporated in vacuo
customthe residue was purified by silica gel column chromatography
washeluting with 40-60% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record: ord-2bee90d555524516ab1e2fed9718c21c
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039500B2

Reaction notes

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