3,4-Dichloroaniline → DU 19111

HRID 261480Notes

Reaction equation

HRID 261480 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH2:18]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[C:4]([NH:6][C:7]([NH:18][C:17]1[CH:19]=[CH:20][C:21]([Cl:22])=[C:15]([Cl:14])[CH:16]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 129127392,6-Dichlorobenzoyl isocyanate

Product 1

HCID 169688DU 19111

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

35 g of 2,6-dichlorobenzoylisocyanate in 100 ml of dry benzene are added drop by drop, with stirring and cooling, to a solution of 24.3 g of 3,4-dichloroaniline in 200 ml of dry benzene. Much heat is evolved and a precipitate is formed which is drawn off while hot and then is washed with hot benzene. The resulting N-(2,6-dichlorobenzoyl)-N'-(3,4-dichlorophenyl)-urea is pure, as is shown by thin layer chromatography (with ethylacetate as the solvent). If desired, the product may be recristallized from acetonitrile. Melting point 238° K.

Workup

  1. temperatureMuch heat
  2. customa precipitate is formed which
  3. washthen is washed with hot benzene

Sources & evidence

ORD record
ord-bd098ea07f574f6b86ba1c70a7ec3263
Source dataset
uspto-grants-1979_08
Patent number
US04166124

Reaction notes

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