Allyl bromide → N-allyl-N-methyl-4-amino-2-oxo-3-pentenesulfonamide

HRID 1252252Notes

Reaction equation

HRID 1252252 reaction equation
[NH2:1][C:2]([CH3:12])=[CH:3][C:4](=[O:11])[CH2:5][S:6]([NH:9][CH3:10])(=[O:8])=[O:7].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([N:9]([CH3:10])[S:6]([CH2:5][C:4](=[O:11])[CH:3]=[C:2]([NH2:1])[CH3:12])(=[O:8])=[O:7])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 736638084-amino-N-methyl-2-oxo-3-pentenesulfonamide

Product 1

HCID 73663809N-allyl-N-methyl-4-amino-2-oxo-3-pentenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In accordance with the procedure described in Example 7, a solution of 3.8 g of 4-amino-N-methyl-2-oxo-3-pentenesulfonamide and 2.5 ml of allyl bromide in 50 ml of dimethylformamide was treated with 6 g of potassium carbonate and the mixture was stirred intensively at room temperature for 7 hours. The product was firstly chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (4:1) as the elution agent and then recrystallized from methylene chloride/ether. There were obtained 3.3 g of N-allyl-N-methyl-4-amino-2-oxo-3-pentenesulfonamide in the form of colorless crystals, m.p. 86°-89°.

Workup

  1. customThe product was firstly chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (4:1) as the elution agent
  2. customrecrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-2600abd8c1624937bae69247c52d2514
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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