Sodium Bicarbonate → N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazol-2-amine

HRID 1698607Notes

Reaction equation

Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:28]=[C:27]([CH3:29])[C:25]([NH2:26])=[C:24]([O:30][CH3:31])[CH:23]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[Cl:21][C:22]1[CH:28]=[C:27]([CH3:29])[C:25]([NH:26][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([F:13])([F:14])[F:15])[C:4]=3[N:3]=2)=[C:24]([O:30][CH3:31])[CH:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole (290 mg, 0.95 mmol), 4-chloro-2-methoxy-6-methylaniline (491 mg, 2.86 mmol) and N-methyl-2-pyrrolidinone (3 drops) was heated at 110° C. for 72 h. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel with a 10% ethyl acetate/n-hexane and recrystallized from diisopropylether/n-hexane to give 140 mg (0.32 mmol, 34%) of the title compound as a white powder.

Workup

extractionextracted with ethyl acetate
washThe extracts were washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel with a 10% ethyl acetate/n-hexane
customrecrystallized from diisopropylether/n-hexane

Sources & evidence

ORD record: ord-69aa83ef91b243eb8493850b85b3c0e6
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163935B2

Reaction notes

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