tert-Butylsulfinamide, (R)-(+)- → (NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 219173

Reaction equation

HRID 219173 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:17]\[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 141091094-Bromo-2-chlorobenzaldehyde

Product 1

HCID 57691068(NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

A suspension of 4-bromo-2-chlorobenzaldehyde (1150 mg, 5240 μmol), (r)-(+)-2-methyl-2-propanesulfinamide (1588 mg, 13100 μmol), copper(ii) sulfate (696.4 μl, 15720 μmol) in DCM (10 mL) was stirred at 37° C. for 78 h. Reaction filtered through Celite, and solid washed repeatedly with DCM. Filtrate concentrated then purified on silica (80 g) eluting product with 0>30% of EtOAc/Hex. MS (ESI pos. ion) m/z: 322/324 (MH+). Calc'd exact mass for C11H13BrClNOS: 321/323.

Workup

  1. customReaction
  2. filtrationfiltered through Celite, and solid
  3. washwashed repeatedly with DCM
  4. concentrationFiltrate concentrated
  5. customthen purified on silica (80 g)
  6. washeluting product with 0>30% of EtOAc/Hex

Sources & evidence

ORD record
ord-afae97caf5a54d0fad555628d65671b3
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Linked notes

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