Water → Methyl N-(2,6-dichloro-4-(trifluoromethyl)phenyl)sulfamoylcarbamate

HRID 1522078Notes

Reaction equation

Cl[S:2]([NH:5][C:6](=[O:9])[O:7][CH3:8])(=[O:4])=[O:3].[Cl:10][C:11]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:12]=1[NH2:13].C(N(CC)CC)C.O>C(Cl)Cl>[Cl:10][C:11]1[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[C:14]([Cl:22])[C:12]=1[NH:13][S:2]([NH:5][C:6](=[O:9])[O:7][CH3:8])(=[O:4])=[O:3]

Participants

Conditions

Temperature: -20 °C

Procedure

Methyl chlorosulfonylcarbamate (27.90 g, 0.16 mol) was dissolved in CH2Cl2 (100 mL) and cooled to −20° C. To the solution of methyl chlorosulfonylcarbamate, was dropwisely added 2,6-dichloro-4-(trifluoromethyl)aniline (2.50 g, 10.7 mmol) and triethylamine (2.53 g, 32.1 mmol) in CH2Cl2 (70 mL) and agitated for 12 hr at room temperature. The reaction mixture was added with water (100 mL) for extraction to obtain the organic layer. The resultant was dried over MgSO4, concentrated under reduced pressure, and purified by column chromatography (hexane:ethyl acetate=7:3), giving the compound of interest (2.11 g, 6%, yellow solid). 1H NMR (300 MHz, CDCl3): δ 7.57 (s, 2H), 3.84 (s, 3H).

Workup

customto obtain the organic layer
dry with materialThe resultant was dried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by column chromatography (hexane:ethyl acetate=7:3)
customgiving the compound of interest (2.11 g, 6%, yellow solid)

Sources & evidence

ORD record: ord-b5e83878c844419aa68f9bab43af3662
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073906B2

Reaction notes

Loading…