Dimethylamine → N-[(4-Bromophenyl)(dimethylamino)oxo-lambda6-sulfanylidene]-2,2,2-trifluoroacetamide

HRID 1485630Notes

Reaction equation

[CH:1]([N:4](CC)[CH:5](C)C)(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[O:18])=[CH:13][CH:12]=1.ClN1C(=O)CCC1=O.CNC>C(#N)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([N:4]([CH3:5])[CH3:1])(=[O:18])=[N:19][C:20](=[O:25])[C:21]([F:22])([F:23])[F:24])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -10 °C

Procedure

N,N-Diisopropylethylamine (14 μL) is added to a mixture of N-(4-bromobenzenesulfinyl)-2,2,2-trifluoroacetamide (50 mg), N-chlorosuccinimide (25 mg), and dimethylamine solution (2 M in tetrahydrofuran; 0.16 mL) in acetonitrile (2 mL) at −10° C. under an argon atmosphere. The reaction mixture is stirred at −10° C. for 15 min, warmed to room temperature and stirred for 3 h. The reaction mixture is extracted with dichloromethane and the combined extracts are washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound. The crude product is used for the next step without further purification. LC (method 1): tR=1.07 min; Mass spectrum (ESI+): m/z=359, 361 [M+H]+.

Workup

temperaturewarmed to room temperature
stirringstirred for 3 h
extractionThe reaction mixture is extracted with dichloromethane
washthe combined extracts are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-913eb6ef83934e7997bfb7fabd84da18
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422312B2

Reaction notes

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