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

HRID 1415364Notes

Reaction equation

HRID 1415364 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH:5]1([C:12]2[S:16][C:15]([NH2:17])=[N:14][N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C(OCC)(=O)C>[CH:5]1([C:12]2[S:16][C:15]([N:17]=[C:1]=[O:2])=[N:14][N:13]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 214478325-Cycloheptyl-2-amino-1,3,4-thiadiazole

Product 1

HCID 214819185-Cycloheptyl-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-cycloheptyl-2-amino-1,3,4-thiadiazole (45 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 filtered to recover 48 grams of a white solid. This solid was recrystallized for dimethyl formamide to yield the desired product 5-cycloheptyl-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 48 grams of a white solid
  7. customThis solid was recrystallized for dimethyl formamide

Sources & evidence

ORD record
ord-f97b6f174a3a457b814425d0be9d6171
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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