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

HRID 66939

Reaction equation

HRID 66939 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]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18])([O-:13])=[O:12]>C1(C)C(C)=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][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

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415185-(3-Nitrobenzamido)-3-Trichloromethyl-1,2,4-ThiadiazoleYield 69.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 21.8 g (0.1 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 18.6 g (0.1 mole) 3-nitrobenzoyl chloride in 250 ml xylene was heated at reflux for 20 hours. Unreacted starting amino compound was recovered by cooling the reaction mixture and filtering the resulting precipitate. The filtrate was concentrated in vacuo and the residue recrystallized from xylene. After washing with petroleum ether, 25.4 g (69% yield) of pure product was obtained; m.p. 198° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customUnreacted starting amino compound was recovered
  3. temperatureby cooling the reaction mixture
  4. filtrationfiltering the resulting precipitate
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue recrystallized from xylene
  7. washAfter washing with petroleum ether

Sources & evidence

ORD record
ord-de6e7a9e35cd4ea48025e0a704ebed64
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Linked notes

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