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

HRID 1920741Notes

Reaction equation

HRID 1920741 reaction equation
C1(C=O)CC1.[CH:6]1([CH:9]=[N:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH2:8][CH2:7]1>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH:6]1([CH:9]=[N:10][S@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 66701339N-(Cyclopropylmethylene)-2-methylpropane-2-sulfinamide

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), 2-methyl-2-propanesulfinic acid 1-cyclopropyl-methylideneamide (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-d723796de88247eeb22227e26451ddf4
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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