Dimethylformamide → HCID 54723586, compound

HRID 1764453Notes

Reaction equation

HRID 1764453 reaction equation
CN(C1C=CC=CC=1)[C:3]([N:5]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[S:6]1(=[O:8])=[O:7])=O.C[O-].[Na+].[CH3:26][N:27]([CH3:30])[CH:28]=[O:29]>>[OH:16][C:15]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:6](=[O:7])(=[O:8])[NH:5][C:3]=1[C:28]([N:27]([CH3:30])[C:26]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)=[O:29]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 70619046HCID 70619046, compound

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-4947a4a5da6f4b2397809df62648542a
Source dataset
uspto-grants-1978_09
Patent number
US04116964

Reaction notes

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