Phosgene → 2-t-Butyl-1,3,4-thiadiazol-5-yl Isocyanate

HRID 441459Notes

Reaction equation

HRID 441459 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]([C:9]1[S:13][C:12]([NH2:14])=[N:11][N:10]=1)([CH3:8])([CH3:7])[CH3:6]>C(OCC)(=O)C>[C:5]([C:9]1[S:13][C:12]([N:14]=[C:1]=[O:2])=[N:11][N:10]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 170170Buthidazolamine

Product 1

HCID 64524562-t-Butyl-1,3,4-thiadiazol-5-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-t-butyl-2-amino-1,3,4-thiadiazole (10 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 then filtered to recover the desired product 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer as a solid having a melting point of 261° to 263° C.

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 then filtered
  6. customto recover the desired product 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer as a solid

Sources & evidence

ORD record
ord-68fa551909ac4f4baa3fd12798e1d6ff
Source dataset
uspto-grants-1977_08
Patent number
US04040812

Reaction notes

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