Phenyl isocyanate → 1-(2-Benzoyl-4-chlorophenyl)-3-phenylurea

HRID 128031Notes

Reaction equation

HRID 128031 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>C(Cl)Cl>[C:13]([C:12]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:11]=1[NH:10][C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9])(=[O:14])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 44239461-(2-Benzoyl-4-chlorophenyl)-3-phenylureaYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 13.1 g (0.11 mole) of phenyl isocyanate and 23.17 g (0.1 mole) of 2-amino-5-chlorobenzophenone in 70 ml of methylene chloride was refluxed for 20 hr, and then evaporated to dryness under reduced pressure. The residue was recrystallized from ethanol to give 31.71 g (90%) of 1-(2-benzoyl-4-chlorophenyl)-3-phenylurea as colorless crystals: mp 145°-147°; 1H nmr (DMSO-d6) δ6.7-8.3 ppm (m, 13H), 9.43 ppm (d, J=7 Hz, 1H, exD2O) and 10.25 ppm (s, 1H, exD2O); 13C nmr (DMSO-d6) δ152.2 ppm (NHCO) and 195.5 ppm (C=O).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e4943f47562c43da92590901a9b632c2
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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