Phosgene → 1,3,4-Thiadiazole, 2-isocyanato-5-(trifluoromethyl)-, dimer

HRID 839783Notes

Reaction equation

HRID 839783 reaction equation
[C:1](Cl)(Cl)=[O:2].[F:5][C:6]([F:14])([F:13])[C:7]1[S:11][C:10]([NH2:12])=[N:9][N:8]=1>C(OCC)(=O)C>[C:1](=[O:2])=[N:12][C:10]1[S:11][C:7]([C:6]([F:14])([F:13])[F:5])=[N:8][N:9]=1.[C:1](=[O:2])=[N:12][C:10]1[S:11][C:7]([C:6]([F:14])([F:13])[F:5])=[N:8][N:9]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 826341,3,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-

Product 1

HCID 768718351,3,4-Thiadiazole, 2-isocyanato-5-(trifluoromethyl)-, dimer

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A saturated solution of phosgene in ethyl acetate (100 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 5-trifluoromethyl-2-amino-1,3,4-thiadiazole (10 grams) in ethyl acetate (300 ml) is added to the reaction vessel, and the resulting mixture is stirred for a period of about 16 hours, resulting in the formation of a precipitate. The reaction mixture is then purged with nitrogen gas to remove unreacted phosgene. The purged mixture is then filtered to recover the desired product 5-trifluoromethyl-1,3,4-thiadiazol-2-yl isocyanate dimer.

Workup

  1. customequipped with a mechanical stirrer
  2. customresulting in the formation of a precipitate
  3. customThe reaction mixture is then purged with nitrogen gas
  4. customto remove unreacted phosgene
  5. filtrationThe purged mixture is then filtered
  6. customto recover the desired product 5-trifluoromethyl-1,3,4-thiadiazol-2-yl isocyanate dimer

Sources & evidence

ORD record
ord-fbd01fb441a14bbba5f0046c700b3572
Source dataset
uspto-grants-1978_06
Patent number
US04097486

Reaction notes

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