Thiophosgene → 2-Chloro-5-phenyl-1,3,4-thiadiazole

HRID 1076998Notes

Reaction equation

HRID 1076998 reaction equation
[C:1]1([C:7]2N=N[NH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](Cl)([Cl:14])=[S:13]>C(COC)OC>[Cl:14][C:12]1[S:13][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 874255-Phenyl-1H-tetrazole

Product 1

HCID 2531452-Chloro-5-phenyl-1,3,4-thiadiazoleYield 41.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 74.4 g (0.50 mole) of 5-phenyl-2H-tetrazole and 74.0 g (0.65 mole) of thiophosgene in 550 ml of dimethoxyethane was allowed to reflux overnight. The reaction mixture was cooled and filtered. The filtrate was taken to dryness at reduced pressure and the resulting residue leached with two 220-ml portions of hexane. Upon cooling and concentration of the combined hexane portions 40.5 g of the desired product was obtained: mp 82°-84° (lit. 86°-88°).

Workup

  1. temperatureto reflux overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. temperatureUpon cooling

Sources & evidence

ORD record
ord-31c345209c834c1ba86f574ccd76656a
Source dataset
uspto-grants-1976_05
Patent number
US03959301

Reaction notes

Loading…