Benzoyl chloride → 5-Benzamido-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 1156716Notes

Reaction equation

HRID 1156716 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:18])[C:12]1[CH:17]=[CH:16][CH:15]=[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:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 128516015-Benzamido-3-Trichloromethyl-1,2,4-ThiadiazoleYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 10.9 grams (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 14.1 grams (0.1 mole) benzoyl chloride in 200 milliliters xylene was refluxed at about 140° C. for 20 hours. Upon cooling the reaction mixture to -10° C., 13.7 grams (85% yield) pure product precipitated; m.p. 190.5° C.

Sources & evidence

ORD record
ord-1defb461d5e74d5992f4e26ae66bf814
Source dataset
uspto-grants-1982_06
Patent number
US04337081

Reaction notes

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