Phosgene → HCID 178523574, compound

HRID 1249747Notes

Reaction equation

HRID 1249747 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]1([C@H:11]2[CH2:16][CH2:15][C@H:14]([NH2:17])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1.CCOCC>[C:5]1([C@H:11]2[CH2:12][CH2:13][C@H:14]([N:17]=[C:1]=[O:2])[CH2:15][CH2:16]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 178511499HCID 178511499, compound

Product 1

HCID 178523574HCID 178523574, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Phosgene (20% in toluene, 5 ml) was added to a solution of trans-4-phenylcyclohexylamine (500 mg, 2.85 mmol) in toluene (5 ml) under nitrogen at room temperature. The resulting solution was heated at 80° C. for 24 hours. Solvents were then removed under vacuum to leave a solid residue. This residue was dispersed in ether and filtered. The eluent was collected and concentrated to give 379 mg of trans-4-phenylcyclohexylisocyanate as a light yellow oil. IR (film) 2259 cm−1.

Workup

  1. customSolvents were then removed under vacuum
  2. customto leave a solid residue
  3. filtrationfiltered
  4. customThe eluent was collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61fd48a5d3b34be79c0bbd01e4a8cbda
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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