3,5-Dinitrobenzoyl chloride → 5-(3,5-Dinitrobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66941

Reaction equation

[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:17](Cl)=[O:18])([O-:13])=[O:12]>C1(C)C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:17]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)=[O:18])([O-:13])=[O:12]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 10.9 g (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 12.6 g (0.055 mole) 3,5-dinitrobenzoyl chloride in 200 ml toluene was refluxed for 20 hours. The crude product precipitated from the reaction mixture upon cooling to -10° C. After isolation by filtration, the residue was washed with hot petroleum ether and finally recrystallized from methylene chloride to give 17.5 g (85% yield) of pure product; m.p. 197° C.

Workup

customThe crude product precipitated from the reaction mixture
filtrationAfter isolation by filtration
washthe residue was washed with hot petroleum ether
customfinally recrystallized from methylene chloride

Sources & evidence

ORD record: ord-8e93b465b8fa4b39bec5f67f154ba6ef
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04343945

Linked notes

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