Benzyl Bromide → 4-amino-N-benzyl-N-methyl-2-oxo-3-pentenesulfonamide

HRID 1252251Notes

Reaction equation

HRID 1252251 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)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]([CH3:12])=[CH:3][C:4](=[O:11])[CH2:5][S:6]([N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:10])(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 736638084-amino-N-methyl-2-oxo-3-pentenesulfonamide

Product 1

HCID 700450344-amino-N-benzyl-N-methyl-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 3.6 ml of benzyl bromide in 50 ml of dimethylformamide was treated with 6 g of potassium carbonate and the mixture was stirred intensively at room temperature for 9 hours. The product was firstly chromatographed on 300 g of silica gel with ethyl acetate as the elution agent and then recrystallized from isopropanol. There were obtained 3.4 g of 4-amino-N-benzyl-N-methyl-2-oxo-3-pentenesulfonamide in the form of colorless crystals, m.p. 115°-118°.

Workup

  1. customThe product was firstly chromatographed on 300 g of silica gel with ethyl acetate as the elution agent
  2. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-8cb9429ee40943b9b609b38b501c7db4
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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