Phosgene → 5-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate

HRID 258509Notes

Reaction equation

HRID 258509 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH:5]1([C:8]2[S:12][C:11]([NH2:13])=[N:10][N:9]=2)[CH2:7][CH2:6]1>C(OCC)(=O)C>[CH:5]1([C:8]2[S:12][C:11]([N:13]=[C:1]=[O:2])=[N:10][N:9]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 7170215-Cyclopropyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 539755145-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate

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-cyclopropyl-2-amino-1,3,4-thiadiazole (6 grams) in ethyl acetate (100 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 a precipitate. The reaction mixture was then purged with nitrogen gas to remove unreacted phosgene. The purged mixture was filtered to recover the desired product 5-cyclopropyl-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 was then purged with nitrogen gas
  4. customto remove unreacted phosgene
  5. filtrationThe purged mixture was filtered
  6. customto recover the desired product 5-cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate dimer

Sources & evidence

ORD record
ord-3a89f82842114c90918ce4fe00777a6d
Source dataset
uspto-grants-1977_07
Patent number
US04033753

Reaction notes

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