Saccharin → HCID 54723586, compound

HRID 616421Notes

Reaction equation

HRID 616421 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[NH:4]1)(=[O:3])=[O:2].[CH3:13][O-:14].[Na+].[CH3:16][N:17]([CH3:20])[CH:18]=[O:19]>>[OH:14][C:13]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[S:1](=[O:2])(=[O:3])[NH:4][C:5]=1[C:18]([N:17]([CH3:20])[C:16]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1)=[O:19]

Participants

4

Reactant 3

HCID 5143SaccharinHCID 6228DimethylformamideHCID 10942334Sodium Methoxide

Product 1

HCID 54723586HCID 54723586, compound

Procedure

To a solution of 9.9g (0.03 mole) of 2- (N-methyl-N-phenylcarbamoyl)!saccharin in 125ml of dimethylformamide at 35° C is added all at once 4.9g (0.09 mole) of sodium methoxide. A considerable amount of heat is evolved and the mixture turns purple in color. Stirring is continued for one hour and it is poured into ice-water containing excess hydrochloric acid to cause precipitation of 5.5g of a tan solid, mp. 138°-144° C. This is dissolved in dichloromethane and extracted with aqueous sodium carbonate solution. Neutralization of the alkaline layer gives a precipitate which is collected and recrystallized from methanol to give 4.0g of product, mp. 148°-152° C dec.

Workup

  1. temperatureA considerable amount of heat
  2. customprecipitation of 5.5g of a tan solid, mp. 138°-144° C
  3. dissolutionThis is dissolved in dichloromethane
  4. extractionextracted with aqueous sodium carbonate solution
  5. customNeutralization of the alkaline layer gives a precipitate which
  6. customis collected
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3ceab7c53af04b81a05b16f40bbe0d07
Source dataset
uspto-grants-1978_02
Patent number
US04074048

Reaction notes

Loading…