Acetaldehyde → (R)-N-[(1E)-Ethylidene]-2-methylpropane-2-sulfinamide

HRID 246018Notes

Reaction equation

HRID 246018 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]>C(Cl)Cl.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>[CH:8](=[N:7]/[S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])\[CH3:9]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 12995916(R)-N-[(1E)-Ethylidene]-2-methylpropane-2-sulfinamideYield 107.2%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask (R)-2-methyl-propane-2-sulfinic acid amide (4.00 g, 33.0 mmol) was dissolved in CH2Cl2 (14.0 mL). Acetaldehyde (16.7 mL, 297 mmol), MgSO4 (11.9 g, 99.0 mmol) and pyridinium tosylate (415 mg, 1.65 mmol) were added. The reaction mixture was stirred overnight at room temperature, filtered and concentrated to give 5.21 g of (R)-2-methyl-propane-2-sulfinic acid (E)-ethylideneamide as a yellow oil which was used without further purification.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-62373fa8c2c14e4c923c81182c51b751
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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