Phosgene → HCID 21559381, compound

HRID 1578519Notes

Reaction equation

HRID 1578519 reaction equation
[F:1][C:2]([C:7]1[S:8][C:9]([NH2:12])=[N:10][N:11]=1)([F:6])[CH:3]([Cl:5])[Cl:4].[C:13](Cl)(Cl)=[O:14]>ClC1C=CC=CC=1>[F:1][C:2]([C:7]1[S:8][C:9]([N:12]=[C:13]=[O:14])=[N:10][N:11]=1)([F:6])[CH:3]([Cl:4])[Cl:5]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 21559377HCID 21559377, compound

Product 1

HCID 21559381HCID 21559381, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

21.7 g (0.1 mol) of 2-(1',1'-difluoro-2',2'-dichloroethyl)-5-amino-1,3,4-thiadiazole were suspended at room temperature in 500 ml of chlorobenzene, and a solution of 30 g of phosgene in 200 ml of chlorobenzene was rapidly added with agitation. With further agitation and feeding-in of gaseous phosgene, the temperature was raised by 15°C per hour until 110°C were attained (a clear solution was obtained from 60°C onward). The solution was then allowed to cool, nitrogen was passed through the solution to remove the residual phosgene, and the solution was concentrated. A brittle mass remained which became pulverulent on trituration with petroleum ether (boiling point 80°-110°C). By suction-filtration and drying, 19 g (73 %) of 2-(1',1'-difluoro-2',2'-dichloro-ethyl)-5-isocyanato-1,3,4-thiadiazole were obtained. Decomposition temperature: 200°C.

Workup

  1. customwas obtained from 60°C onward)
  2. temperatureto cool
  3. customto remove the residual phosgene
  4. concentrationthe solution was concentrated
  5. filtrationBy suction-filtration
  6. customdrying

Sources & evidence

ORD record
ord-351996210d5e4d62a987fa40cbf0e2ce
Source dataset
uspto-grants-1976_02
Patent number
US03937715

Reaction notes

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