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

HRID 1729884Notes

Reaction equation

HRID 1729884 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-dichloroaniline 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 the 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-10410f693dbf442d8e427f9b38745c04
Source dataset
uspto-grants-1976_11
Patent number
US03989842

Reaction notes

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