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

HRID 66937

Reaction equation

HRID 66937 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][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([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:13][CH:12]=1

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415165-(4-Toluamido)-3-Trichloromethyl-1,2,4-Thiadiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.0 g (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 8.0 g (0.05 mole) 4-toluoyl chloride in 250 ml toluene was heated at reflux for 20 hours. Unreacted amino compound was removed by cooling the reaction mixture and filtering the precipitate. Concentration of the filtrate in vacuo gave the crude product, which was purified by recrystallization from cyclohexane. Yield was 9.1 g (27%); m.p. 127° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customUnreacted amino compound was removed
  3. temperatureby cooling the reaction mixture
  4. filtrationfiltering the precipitate

Sources & evidence

ORD record
ord-941fe4c55371425b876f0a5cbd9052c1
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Linked notes

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