Ammonia → 4-amino-N-methyl-2-oxo-3-pentenesulfonamide

HRID 1252244Notes

Reaction equation

HRID 1252244 reaction equation
[NH3:1].[CH3:2][N:3]1[C:8]([CH3:9])=[CH:7][C:6](=[O:10])[CH2:5][S:4]1(=[O:12])=[O:11]>CO>[NH2:1][C:8]([CH3:9])=[CH:7][C:6](=[O:10])[CH2:5][S:4]([NH:3][CH3:2])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 124708272,3-dimethyl-1,2-thiazin-5(6H)-one 1,1-dioxide

Product 1

HCID 736638084-amino-N-methyl-2-oxo-3-pentenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A moderately rapid stream of dry ammonia was introduced at 20°-25° during 3 hours into a suspension of 10 g of 2,3-dimethyl-1,2-thiazin-5(6H)-one 1,1-dioxide in 100 ml of methanol, whereby a clear pale yellow solution resulted after about 10-15 minutes. Thereupon, the mixture was stirred further at room temperature overnight. The crystallized-out product was filtered off and washed with a small amount of methanol, whereby there were obtained 9.8 g of 4-amino-N-methyl-2-oxo-3-pentenesulfonamide in the form of colorless crystals, m.p. 158°-162°. From the filtrate there were obtained by concentration to about 50 ml an additional 2.2 g of product, mp. 158°-162°, total yield: 12 g.

Workup

  1. customresulted after about 10-15 minutes
  2. filtrationThe crystallized-out product was filtered off
  3. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-d150bee67fb94132b801397a7070f6c4
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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