Acetaldehyde → (S)-N-[(1E)-ethylidene]-2-methylpropane-2-sulfinamide

HRID 246060Notes

Reaction equation

HRID 246060 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH:8](=O)[CH3:9].[O-]S([O-])(=O)=O.[Mg+2].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:8](=[N:7]/[S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])\[CH3:9]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 77058989(S)-N-[(1E)-ethylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flask (S)-2-methyl-propane-2-sulfinic acid amide (1.50 g, 12.4 mmol) was dissolved in CH2Cl2 (6 mL). Acetaldehyde (6.25 mL, 111 mmol), MgSO4 (4.47 g, 37.1 mmol) and pyridinium tosylate (156 mg, 0.62 mmol) were added. The reaction mixture was stirred overnight at room temperature, filtered and concentrated to give (S)-2-methyl-propane-2-sulfinic acid (E)-ethylideneamide as a pale red oil which was used without further purification.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ab8e54b477a54be58970a62ff32565e8
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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