Benzene, 1-chloro-3-isocyanato- → Phenyl-(3-chlorophenylaminocarbonyloxy)-malonic acid diamide

HRID 255478

Reaction equation

HRID 255478 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:11]1([C:17]([OH:24])([C:21]([NH2:23])=[O:22])[C:18]([NH2:20])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)(=O)C.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.[Zn+2]>[C:11]1([C:17]([O:24][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[O:10])([C:21]([NH2:23])=[O:22])[C:18]([NH2:20])=[O:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 131800612-Hydroxy-2-phenylmalonamide

Product 1

HCID 13361940Phenyl-(3-chlorophenylaminocarbonyloxy)-malonic acid diamideYield 55.6%

Reagents, catalysts & solvents 2

HCID 11180Zinc CaprylateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g of zinc octoate and 4.45 g of 3-chlorophenyl isocyanate were added to 8.2 g of phenylhydroxymalonic acid diamide in 30 ml of ethyl acetate and the mixture was kept at 50° C. for 30 minutes. After cooling, the precipitate was filtered off with suction and recrystallised from acetone. 5.6 g of phenyl-(3-chlorophenylaminocarbonyloxy)-malonic acid diamide of melting point 196°-198° C. were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction
  3. customrecrystallised from acetone

Sources & evidence

ORD record
ord-f4aee39cd75a4c03922b1961aa114d69
Source dataset
uspto-grants-1987_10
Patent number
US04698333

Linked notes

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