Acetic Anhydride → 7-[N-acetyl-N-(4-Chlorophenyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235559Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]3[N:16]([CH3:18])[C:15](=[O:19])[N:14]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[C:17]3[N:16]([CH3:18])[C:15](=[O:19])[N:14]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)[C:29](=[O:31])[CH3:30])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-[(4-chlorophenyl)amino]-1-(4-methoxybenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.393 g, 1.0 mmol), pyridine (0.1 ml) and acetic anhydride (10 ml) was heated at 120° C. for 4 days. The mixture was evaporated in vacuo. The residue was diluted with ethyl acetate (50 ml), washed with saturated sodium bicarbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed eluting with 40-50% ethyl acetate/hexanes to give N-(4-chlorophenyl)-N-[1-(4-methoxybenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-4-yl]acetamide (0.388 g, quant.) as an oil.

Workup

customThe mixture was evaporated in vacuo
additionThe residue was diluted with ethyl acetate (50 ml)
washwashed with saturated sodium bicarbonate
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customchromatographed
washeluting with 40-50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-38709787dc564bdfbbd06675dbae8d03
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714009B2

Reaction notes

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