tert-Butylsulfinamide, (R)-(+)- → HCID 89479433, compound

HRID 1850170Notes

Reaction equation

HRID 1850170 reaction equation
[F:1][CH:2]([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([F:11])[CH:4]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][CH:2]([F:12])[C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[N:19]/[S@@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])=[C:5]([F:11])[CH:4]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 739493584-(Difluoromethyl)-2-fluorobenzaldehyde

Product 1

HCID 89479433HCID 89479433, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of 4-(difluoromethyl)-2-fluorobenzaldehyde (162 mg, 0.930 mmol) and (R)-2-methylpropane-2-sulfinamide (124 mg, 1.023 mmol) in DCE (3 mL) was added copper sulfate (223 mg, 1.396 mmol). Reaction mixture was heated in a preheated oil bath to 55° C. for 38 hours. The mixture was allowed to cool to room temperature, filtered through a pad of celites and washed with DCE. Combined filtrates were concentrated under reduced pressure to afford (R,E)-N-(4-(difluoromethyl)-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (266 mg) as a yellow oil, which was used without further purification. LCMS m/z 278.1 (M+H)+, Rt 0.98 min.

Workup

  1. customReaction mixture
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a pad of celites
  4. washwashed with DCE
  5. concentrationCombined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8feb853e9524226a3f14a9e30f7185e
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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