2,4-Dichloroaniline → Ethyl [4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

HRID 1398746Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (708 mg, 2.06 mmol), 2,4-dichloroaniline (1.00 g, 6.19 mmol) and N-methyl-2-pyrrolidinone (0.5 mL) was stirred at 100° C. for 3.5 days. After cooling, the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 3-15% ethyl acetate/n-hexane gradient mixture. The resulting solid was washed with n-hexane to give the title compound (115 mg, 0.245 mmol, 12%) as a colorless solid.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by basic silica gel column chromatography
washeluting with a 3-15% ethyl acetate/n-hexane gradient mixture
washThe resulting solid was washed with n-hexane

Sources & evidence

ORD record: ord-12c9d1f3b5eb4d5db1418db53703dd3e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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