Sodium hydride → N-[5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrobenzoyl]-S,S-dimethyl-sulphoximine

HRID 637254Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

0.48 g of sodium hydride is placed in 10 ml of absolute dimethylformamide. 1.96 g of o-chloro-p-trifluoromethyl-phenol are added dropwise and the mixture is stirred for 1 hour. 2.6 g of N-(5-fluoro-2-nitrobenzoyl)-S,S-dimethyl-sulphoximine are added and the mixture is heated to 100° C. for 90 minutes. The mixture is then cooled, poured on to 100 ml of ice-water and extracted with 50 ml of ethyl acetate. The ethyl acetate phase is washed with water, dried and evaporated, and the residue is purified by chromatography and crystallized from diethyl ether. There is obtained 1 g of N-[5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrobenzoyl]-S,S-dimethyl-sulphoximine, m.p. 122° C.

Workup

temperatureThe mixture is then cooled
extractionextracted with 50 ml of ethyl acetate
washThe ethyl acetate phase is washed with water
customdried
customevaporated
customthe residue is purified by chromatography
customcrystallized from diethyl ether

Sources & evidence

ORD record: ord-5a568fe3b2a34f06928bcc3060d41167
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04556413

Reaction notes

Loading…