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

HRID 258499Notes

Reaction equation

HRID 258499 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 a 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 a 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-904f18dc5242444e9b3e8f96b92eca1c
Source dataset
uspto-grants-1977_07
Patent number
US04033753

Reaction notes

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