1,2-Dimethoxyethane → 1-1,2-Benzisoxazol-3-ylmethyl-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

HRID 1747355Notes

Reaction equation

[H-].[Na+].F[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[N:25][OH:26])[CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([C:21]([CH3:23])=[CH2:22])[C:13]1=[O:24].COCCOC>O>[O:26]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:10]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([C:21]([CH3:23])=[CH2:22])[C:13]2=[O:24])=[N:25]1

Participants

Conditions

Temperature: 85 °C

Procedure

A 25 ml pear-shaped flask was charged with sodium hydride (60% oil dispersion, 68 mg, 1.7 mmol) which was washed with hexanes and then diluted with DME (3 ml). The 1-{2-(2-fluoro-phenyl)-2-[hydroxyimino]-ethyl}-3-isopropenyl-1,3-dihydro-benzimidazol-2-one (0.5 g, 1.5 mmol) was introduced as a DME (3 ml) solution in a dropwise manner. The resulting mixture was warmed to 85° C. for 20 h and cooled to ambient temperature. The reaction was diluted with water and the product was extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 40% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give 0.26 g (55%) of the desired product.

Workup

washwas washed with hexanes
additiondiluted with DME (3 ml)
temperaturecooled to ambient temperature
extractionthe product was extracted into ethyl acetate (2×)
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give the crude product which
customwas purified via column chromatography (silica gel, 40% EtOAc/hexanes)
concentrationconcentrated

Sources & evidence

ORD record: ord-a7f7c0bbdf914745bc5ba83aca003e90
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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