p-Anisoyl chloride → 5-(4-Anisamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66938

Reaction equation

HRID 66938 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[C:11](Cl)(=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>C1(C)C(C)=CC=CC=1>[C:11]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)(=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415175-(4-Anisamido)-3-Trichloromethyl-1,2,4-Thiadiazole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 11.0 g (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 12.8 g (0.08 mole) 4-anisoyl chloride in 200 ml xylene was heated at reflux for 20 hours. Cooling of the reaction mixture resulted in precipitation of the crude product, which was then isolated by filtration. Purification was achieved by washing the crude product with hot hexane. Yield was 12.0 g (82%); m.p. 172° C.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureCooling of the reaction mixture

Sources & evidence

ORD record
ord-c5e879964bea48bfb1cb9bbca35b987c
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Linked notes

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