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

HRID 66935

Reaction equation

HRID 66935 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])[C:12]([C:17](Cl)=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.C1(C)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:11]1([CH3:20])[C:12]([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:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 702762-Methylbenzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415145-(2-Toluamido)-3-Trichloromethyl-1,2,4-ThiadiazoleYield 35.1%

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) 2-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. Following recrystallization for toluene, 11.8 g (35% yield) of pure product was otained; m.p. 170° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customthe resulting precipitate removed by filtration

Sources & evidence

ORD record
ord-40e39dbc987749c18435765ac008b42e
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Linked notes

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