2,6-Dichlorobenzoyl chloride → 5-(2,6-Dichlorobenzamido)-3-Trichloromethyl-1,2,4-Thiadiazole

HRID 66944

Reaction equation

HRID 66944 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:13]=1[C:14](Cl)=[O:15]>C1C(Cl)=CC=C(Cl)C=1>[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:13]=1[C:14]([NH:1][C:2]1[S:6][N:5]=[C:4]([C:7]([Cl:10])([Cl:9])[Cl:8])[N:3]=1)=[O:15]

Participants

4

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 6028483-(Trichloromethyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 130415235-(2,6-Dichlorobenzamido)-3-Trichloromethyl-1,2,4-ThiadiazoleYield 22%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

A solution of 22.0 g (0.1 mole) 5-amino-3-trichloromethyl-1,2,4-thiadiazole and 20.1 g (0.1 mole) 2,6-dichlorobenzoyl chloride was refluxed for 8 hours in 200 ml dichlorobenzene. After filtration, the crude product precipitated from the filtrate upon standing. Recrystallization from toluene gave 8.6 g (22% yield) of pure product; m.p. 209° C.

Workup

  1. filtrationAfter filtration
  2. customthe crude product precipitated from the filtrate
  3. customRecrystallization from toluene

Sources & evidence

ORD record
ord-052451e8e991401cb49c193ee700dc5f
Source dataset
uspto-grants-1982_08
Patent number
US04343945

Linked notes

Loading…