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

HRID 1605798Notes

Reaction equation

HRID 1605798 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]([C:9]1[S:10][C:11]([NH2:14])=[N:12][N:13]=1)([CH3:8])([CH3:7])[CH3:6]>C(OCC)(=O)C>[C:5]([C:9]1[S:10][C:11]([N:14]=[C:1]=[O:2])=[N:12][N:13]=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 2-t-butyl-5-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 2-t-butyl-1,3,4-thiadiazol-5-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 then filtered
  6. customto recover the desired product 2-t-butyl-1,3,4-thiadiazol-5-yl isocyanate dimer

Sources & evidence

ORD record
ord-a222627382a547f2a1cd3d71a2c22192
Source dataset
uspto-grants-1976_04
Patent number
US03951640

Reaction notes

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