Acetaldehyde → (E)-N-ethylidene-2-methylpropane-2-sulfinamide

HRID 1058263Notes

Reaction equation

HRID 1058263 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH:8](=O)[CH3:9]>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[CH:8](=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH3:9]

Participants

5

Reactant 2

HCID 177AcetaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 73164120(E)-N-ethylidene-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-(−)-2-methyl-2-propanesulfinamide (1.0 g, 8.25 mmol) and acetaldehyde (2.0 mL, 35.61 mmol) in dichloromethane (20 mL) at ambient temperature under nitrogen atmosphere was added CuSO4 (2.9 g, 18.15 mmol). The mixture was stirred at ambient temperature for 18 h. The reaction was filtered through celite and the filtrate solvent was removed under reduced pressure. N-ethylidene-2-methyl-2-propanesulfinamide was obtained as a clear colorless oil (1.18 g; 1H NMR, 400 MHz, CDCl3, 8.8 ppm (q, 11H), 2.24 ppm (d, 3H), 1.2 ppm (s, 9H)).

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe filtrate solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-68baf1705349404e9244b2c0dde66ce0
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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