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

HRID 436835Notes

Reaction equation

HRID 436835 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) was charged into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 5-trifluoromethyl-2-amino-1,3,4-thiadiazole (45 grams) in ethyl acetate (300 ml) was added to the reaction vessel and the resulting mixture was stirred for a period of about 16 hours resulting in the formation of precipitate. The reaction mixture was then purged with nitrogen gas to remove unreacted phosgene. The purged mixture was filtered to recover 48 grams of a white solid. This solid was recrystallized from dimethyl formamide to yield 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 precipitate
  3. customThe reaction mixture was then purged with nitrogen gas
  4. customto remove unreacted phosgene
  5. filtrationThe purged mixture was filtered
  6. customto recover 48 grams of a white solid
  7. customThis solid was recrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-47d9212665ab428f8482ee7eb4ee81cb
Source dataset
uspto-grants-1977_06
Patent number
US04028375

Reaction notes

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