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

HRID 1995604Notes

Reaction equation

HRID 1995604 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-050c8f6ece1b4de08088d9f8846a5e34
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

Loading…