Phosgene → HCID 23042021, compound

HRID 2166086Notes

Reaction equation

HRID 2166086 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[O:5].[C:20](Cl)(Cl)=[O:21]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[C:4]1[O:5][C:20](=[O:21])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:6]=1

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 23042016HCID 23042016, compound

Product 1

HCID 23042021HCID 23042021, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
59 °C

Procedure

39 g (0.13 mol) of 2-chloro-6-fluoro-N'-(o-chlorophenyl)-benzhydrazide are treated with a solution of 40 g (0.40 mol) of phosgene in 275 ml of toluene and the mixture is heated to reflux temperature (internal temperature 59° C.) for 2.5 hours. A further 13 g (0.13 mol) of phosgene in 70 ml of toluene are added thereto and the reaction mixture is heated to reflux temperature for a further 2.5 hours. The excess phosgene and toluene are distilled off, and the residue is taken up in 500 ml of diethyl ether and the solution is washed with semisaturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After recrystallization of the crude product from a mixture of diethyl ether and n-hexane there is obtained pure 5-(2-chloro-6-fluorophenyl)-3-(2-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one, m.p. 92°-95° C.; IR spectrum: 1790 cm-1 ; mass spectrum: 324(12), 280 (10), 125(100).

Workup

  1. temperaturethe mixture is heated
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux temperature for a further 2.5 hours
  4. distillationThe excess phosgene and toluene are distilled off
  5. washthe solution is washed with semisaturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customAfter recrystallization of the crude product
  9. additionfrom a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-a8eb269c61794a6c9d857cec7fb63463
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

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