3,4-Dichloroaniline → 1-(2,6-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea

HRID 597331Notes

Reaction equation

HRID 597331 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].[C:12]([SH:14])#[N:13].N.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Cl:24])[NH2:20]>CC(C)=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([NH:13][C:12]([NH:20][C:19]1[CH:21]=[CH:22][C:23]([Cl:24])=[C:17]([Cl:16])[CH:18]=1)=[S:14])=[O:5]

Participants

6

Reactant 3

HCID 72573,4-DichloroanilineHCID 783922,6-Dichlorobenzoyl chlorideHCID 13417437Amthio

Product 1

HCID 190064161-(2,6-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

10.5 g of 2.6-dichlorobenzoylchloride are added drop by drop with stirring to a solution of 3.8 g of ammonium rhodanide in 15 ml of acetone. After boiling for 15 minutes the reaction mixture is added drop by drop to a solution of 8.1 g of 3,4-dichloraniline in 15 ml of acetone. After stirring for 30 minutes the reaction mixture is poured in water and extracted with ether. The ethereal solution is dried and concentrated by evaporation and the residue is taken up in benzene. After working up and decrystallizing from benzene 1.3 g of superscribed substance is obtained. Melting point 240° C.

Workup

  1. extractionextracted with ether
  2. customThe ethereal solution is dried
  3. concentrationconcentrated by evaporation
  4. customis obtained

Sources & evidence

ORD record
ord-5a04eba62e874a9d908cbc2ec4ef7016
Source dataset
uspto-grants-1977_03
Patent number
US04013717

Reaction notes

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