Sodium Chloride → N-[1-Cyclopropyl-2,2-difluoro-2-(phenylsulfonyl)ethyl]-2-methyl-2-propanesulfinamide
Reaction equation
[CH:1]1(/[CH:4]=[N:5]/[S:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[CH2:3][CH2:2]1.[F:12][CH:13]([F:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Na+].[Cl-]>C1COCC1>[CH:1]1([CH:4]([NH:5][S:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:13]([F:12])([F:23])[S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH2:2][CH2:3]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-[(1E)-cyclopropylmethylene]-2-methylpropane-2-sulfinamide (1.0 g, 5.8 mmol) and [(difluoromethyl)sulfonyl]benzene (1.1 g, 5.8 mmol) in THF (60 mL) was added dropwise NaHMDS (2 M, 4 mL, 8.2 mmol) at −78° C. The reaction mixture was stirred at this temperature for 2 h. A saturated NaCl solution (60 mL) was added to the reaction mixture to quench the reaction at −78° C. After warmed to room temperature, the mixture was extracted with EtOAc. The combined organic phases were dried, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, 2H); 7.60 (t, 1H); 7.48 (d, 2H); 3.48 (d, 1H); 1.06-1.10 (m, 1H); 1.05 (s, 9H); 0.45-0.75 (m, 4H).
Workup
- customto quench
- customthe reaction at −78° C
- extractionthe mixture was extracted with EtOAc
- customThe combined organic phases were dried
- concentrationconcentrated
- custompurified by flash chromatography
Sources & evidence
- ORD record
- ord-94202cccd19b4ba8872463f484d9f6f8
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431569B2
Reaction notes
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