4-Nitrobenzoyl chloride → 5-(4-Nitrobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66940Notes

Reaction equation

HRID 66940 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:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12]>C1(C)C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:1][C:2]2[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=2)=[O:19])=[CH:21][CH:22]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415195-(4-Nitrobenzamido)-3-Trichloromethyl-1,2,4-ThiadiazoleYield 73.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10.9 g (0.05 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 10.2 g (0.055 mole) 4-nitrobenzoyl chloride in 200 ml toluene was heated at reflux for 20 hours. Upon cooling to room temperature, the crude product precipitated from the reaction mixture and was isolated by filtration. After washing with hexane, 13.5 g (73% yield) of pure product was obtained; m.p. 214° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customthe crude product precipitated from the reaction mixture
  3. customwas isolated by filtration
  4. washAfter washing with hexane

Sources & evidence

ORD record
ord-cf535115d4a34be684be0052ae84a514
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Reaction notes

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