Phosphorus oxychloride → Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

HRID 1698591Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=O)[NH:14][C:10]=2[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][C:13]1[N:12]([CH3:16])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]=2[N:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (1.30 g, 4.70 mmol) and phosphoryl chloride (10 ml) was heated at 100° C. for 3 h. The mixture was diluted with toluene and concentrated in vacuo to remove excess reagent. The residue was diluted with aqueous saturated sodium bicarbonate 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 column silica gel with a 10% ethyl acetate/n-hexane to give 1.18 g (4.00 mmol, 85%) of the title compound as a colorless oil.

Workup

concentrationconcentrated in vacuo
customto remove excess reagent
additionThe residue was diluted with aqueous saturated sodium bicarbonate
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 column silica gel with a 10% ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-703d12d38d9b4302aa5220d221c67258
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163935B2

Reaction notes

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