2,4-Dichlorobenzoyl chloride → 5-(2,4-Dichlorobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66945Notes

Reaction equation

HRID 66945 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[Cl:11][C:12]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>C1(C)C(C)=CC=CC=1>[Cl:11][C:12]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:13]=1[C:14]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)=[O:15]

Participants

4

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415245-(2,4-Dichlorobenzamido)-3-Trichloromethyl-1,2,4-ThiadiazoleYield 69.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 10.9 g (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 20.9 g (0.10 mole) 2,4-dichlorobenzoyl chloride was refluxed in 200 ml xylene for 20 hours. The reaction mixture was concentrated in vacuo and the resulting residue extracted with benzene. Addition of hexane resulted in precipitation of 13.6 g (69% yield) pure product; m.p. 136° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe resulting residue extracted with benzene
  3. additionAddition of hexane

Sources & evidence

ORD record
ord-5ed551a71a4646b6861ec463374c3df0
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Reaction notes

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