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Phosgene → HCID 53797236, compound

HRID 596742
Notes
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Reaction equation

HRID 596742 reaction equation
[C:1](Cl)(Cl)=[O:2].[Cl:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[S:16][C:15]([NH2:17])=[N:14][N:13]=2)[CH2:8][CH2:7]1>C(OCC)(=O)C>[Cl:5][CH:6]1[CH2:7][CH2:8][CH:9]([C:12]2[S:16][C:15]([N:17]=[C:1]=[O:2])=[N:14][N:13]=2)[CH2:10][CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 214478445-(4-Chlorocyclohexyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 53797236HCID 53797236, compound

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-(4-Chlorocyclohexyl)-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 to yield the desired product 5-(4-chlorocyclohexyl)-1,3,4-thiadiazol-2-yl isocyanate dimer.

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

Sources & evidence

ORD record
ord-079af2be69de4234b7779778648f8865
Source dataset
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04012223

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes