p-Toluenesulfonyl isocyanate → HCID 13361939, compound

HRID 255477Notes

Reaction equation

HRID 255477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:16])([C:13]([NH2:15])=[O:14])[C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17]1([CH3:29])[CH:22]=[CH:21][C:20]([S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([O:16][C:27]([NH:26][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:29])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[O:28])([C:10]([NH2:12])=[O:11])[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 158916Propanediamide, 2-(3,4-dichlorophenyl)-2-hydroxy-

Product 1

HCID 13361939HCID 13361939, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

26.3 g of 3,4-dichlorophenylhydroxymalonic acid diamide were dissolved in 350 ml of ethyl acetate at 65° C., and a solution of 19.7 g of p-toluenesulphonyl isocyanate was slowly added. After the mixture had been kept at 70° C. for 1 hour, it was cooled and filtered off with suction. 14 g of 3,4-dichlorophenyl-p-toluenesulphonylaminocarbonyloxy-malonic acid diamide (melting point 178° C., decomposition) were obtained. Further product was to be isolated from the mother liquor.

Workup

  1. temperatureit was cooled
  2. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-835faee3b63e4e5785d60e6afe1614e6
Source dataset
uspto-grants-1987_10
Patent number
US04698333

Reaction notes

Loading…