Cyclopropanecarboxaldehyde → (S,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamide

HRID 222786

Reaction equation

HRID 222786 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[CH3:6][C:7]([S@@:10]([NH2:12])=[O:11])([CH3:9])[CH3:8]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH:1]1([CH:4]=[N:12][S@:10]([C:7]([CH3:9])([CH3:8])[CH3:6])=[O:11])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 67007580(S,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamideYield 95%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to a general procedure described by G. Liu, D. A. Cogan, T. D. Owens, T. P. Tang, and J. A. Ellman J. Org. Chem. 1999, 64, 1278: A mixture of cyclopropanecarboxaldehyde (35.0 g, 0.5 mol), (S)-(−)-2-methyl-2-propanesulfinamide (30 g, 0.25 mol) and anhydrous CuSO4 (120 g, 0.75 mol) in CH2Cl2 (1500 mL) was stirred at room temperature overnight. The reaction mixture was filtered and evaporated to give the title compound (39 g, yield 95%), which was used in the next step without further purification.

Workup

  1. customThe title compound was prepared
  2. filtrationThe reaction mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-33e946aeab894b1388f17fba0ad828fe
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Linked notes

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