Hydrochloric Acid → 3-(2,6-Dichlorobenzoyl)-1-(p-chlorophenyl)-hydantoin

HRID 847467

Reaction equation

HRID 847467 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:8])=[O:5].[C:22](Cl)(=O)[C:23](Cl)=[O:24].NC(N)=O.Cl>ClCCCl>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([N:6]1[C:23](=[O:24])[CH2:22][N:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C:7]1=[O:8])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 65578Oxalyl chlorideHCID 923002,6-dichloro-N-(((4-chlorophenyl)amino)carbonyl)benzamide

Product 1

HCID 190064153-(2,6-Dichlorobenzoyl)-1-(p-chlorophenyl)-hydantoin

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

10.3 g of N-(2,6-dichlorobenzoyl)-N'-(p-chlorophenyl)-urea are boiled in 100 ml of dry 1,2-dichloroethane containing 3 ml of oxalylchloride for 24 hours. The urea dissolves with the evolution of hydrochloric acid. After concentration by evaporation and after the addition of 25 ml of ligroin the residue becomes crystalline. The substance mauy be recrystallized from 30 mls of benzene. Melting point 157° C. Yield 8 g.

Workup

  1. concentrationAfter concentration
  2. customby evaporation
  3. additionafter the addition of 25 ml of ligroin the residue
  4. customThe substance mauy be recrystallized from 30 mls of benzene

Sources & evidence

ORD record
ord-1d4e2ea2bb504f7b8f8c05fc2fff3709
Source dataset
uspto-grants-1992_08
Patent number
US05142064

Linked notes

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