m-Chloroperbenzoic acid → HCID 67980099, compound

HRID 1403114Notes

Reaction equation

[F:1][CH:2]([F:26])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([S:20][CH3:21])[N:9]=2)[C:6]2[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=2[N:4]=1.ClC1C=CC=C(C(OO)=[O:35])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[F:26][CH:2]([F:1])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([S:20]([CH3:21])=[O:35])[N:9]=2)[C:6]2[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=2[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(difluoromethyl)-1-[2-(methylsulfanyl)-6-morpholin-4-ylpyrimidin-4-yl]-1H-benzimidazole (3 g) in dichloromethane (60 mL) was added m-chloroperbenzoic acid (75% wet) (1.9 g) under ice-cooling, and the mixture was stirred at 0° C. for 15 minutes. To the reaction mixture was added a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (chloroform:methanol) to obtain 2-(difluoromethyl)-1-[2-(methylsulfinyl)-6-morpholin-4-ylpyrimidin-4-yl]-1H-benzimidazole (2.8 g) as a white amorphous substance.

Workup

temperaturecooling
extractionfollowed by extraction with dichloromethane
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record: ord-995a86c1d58b43d68169695635799f11
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912180B2

Reaction notes

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