3-Methylbenzoyl chloride → 5-(3-Toluamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66936

Reaction equation

HRID 66936 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]1([CH3:20])[CH:16]=[CH:15][CH:14]=[C:13]([C:17](Cl)=[O:18])[CH:12]=1>C1(C)C(C)=CC=CC=1>[C:11]1([CH3:20])[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:1][C:2]2[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=2)=[O:18])[CH:12]=1

Participants

4

Reactant 2

HCID 743753-Methylbenzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415155-(3-Toluamido)-3-Trichloromethyl-1,2,4-ThiadiazoleYield 12%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 22.0 g (0.1 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 16.0 g (0.1 mole) 3-toluoyl chloride in 250 ml xylene was heated at reflux for 20 hours. The reaction mixture was cooled to room temperature and the resulting precipitate removed by filtration. The crude product was washed with petroleum ether and then recrystallized twice from toluene to obtain 4.0 g (12% yield) of pure product; m.p. 142° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customthe resulting precipitate removed by filtration
  3. washThe crude product was washed with petroleum ether
  4. customrecrystallized twice from toluene

Sources & evidence

ORD record
ord-0ee1bf474793456ab285a40aa7291cc3
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Linked notes

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