Phosgene → 2-Cyclohexyl-5-isocyanato-1,3,4-thiadiazole

HRID 259139Notes

Reaction equation

HRID 259139 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH:5]1([C:11]2[S:15][C:14]([NH2:16])=[N:13][N:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C(OCC)(=O)C>[CH:5]1([C:11]2[S:15][C:14]([N:16]=[C:1]=[O:2])=[N:13][N:12]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 7326295-Cyclohexyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 539244442-Cyclohexyl-5-isocyanato-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A saturated solution of phosgene in ethyl acetate (500 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer. 5-Cyclohexyl-2-amino-1,3,4-thiadiazole (6 grams) is added to the reaction vessel, and the resulting mixture is stirred and heated at reflux for a period of about 4 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 precipitate. The precipitate is then recrystallized from a dimethyl formamide-water mixture to yield the desired product 5-cyclohexyl-1,3,4-thiadiazol-2-yl isocyanate dimer having a melting point of 237° to 239° C.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureheated
  3. temperatureat reflux for a period of about 4 hours
  4. customresulting in the formation of a precipitate
  5. customThe reaction mixture is then purged with nitrogen gas
  6. customto remove unreacted phosgene
  7. filtrationThe purged mixture is then filtered
  8. customto recover the precipitate
  9. customThe precipitate is then recrystallized from a dimethyl formamide-water mixture

Sources & evidence

ORD record
ord-83bff2834bba43ef8b90b7100e616738
Source dataset
uspto-grants-1977_07
Patent number
US04036848

Reaction notes

Loading…