2,6-Dichlorobenzoyl isocyanate → 1-(2,6-Dichlorobenzoyl)-3-(5-(4-chlorophenyl)-2-pyridyl)urea

HRID 1980308Notes

Reaction equation

HRID 1980308 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:17]=1[C:18]([N:20]=[C:21]=[O:22])=[O:19]>ClCCl>[Cl:15][C:16]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:17]=1[C:18]([NH:20][C:21]([NH:14][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1)=[O:22])=[O:19]

Participants

4

Reactant 2

HCID 129127392,6-Dichlorobenzoyl isocyanateHCID 132426445-(4-Chlorophenyl)pyridin-2-amine

Product 1

HCID 132426451-(2,6-Dichlorobenzoyl)-3-(5-(4-chlorophenyl)-2-pyridyl)ureaYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Chlorophenyl)-2-pyridylamine (0.6 gram), 2,6-dichlorobenzoyl isocyanate (0.8 gram), in a small amount of dichloromethane were reacted at room temperature. A slight exothermic reaction was followed by an almost immediate precipitate. After 3 hours at room temperature, the reaction mixture was cooled in an ice bath and then filtered to give 770 mg of colorless crystals. The identity of the product was confirmed by NMR analysis, m.p. 230°-233° C.

Workup

  1. customA slight exothermic reaction
  2. temperaturethe reaction mixture was cooled in an ice bath
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c2551603214242ed8ee8b902e88b5d48
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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