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

HRID 1962406Notes

Reaction equation

HRID 1962406 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-7c3c41ab14d24d86b05a464466c4db6c
Source dataset
uspto-grants-2013_04
Patent number
US08415373B2

Reaction notes

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