Methane → HCID 86585962, compound

HRID 890362Notes

Reaction equation

HRID 890362 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[C:9]([CH:13]1[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1)([CH3:12])([CH3:11])[CH3:10].C>C(OCC)(=O)C>[N-:19]=[C:4]=[O:3].[C:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 793964-tert-Butylcyclohexylamine

Product 1

HCID 86585962HCID 86585962, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A pre-cooled solution of diphosgene (168.0 mmol) in ethyl acetate was added dropwise via addition funnel into the cold solution of 4-(t-butyl)cyclohexylamine (140.0 mmol) and charcoal (catalytic) in ethyl acetate at −10° C. After the addition, the reaction was heated to reflux overnight, and filtered through a Celite plug. The solution was concentrated to give a thick oil, which was distilled in vacuo to yield 4-(tert-butyl)cyclohexanisocyanate as a clear liquid (48%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux overnight
  4. filtrationfiltered through a Celite plug
  5. concentrationThe solution was concentrated
  6. customto give a thick oil, which
  7. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-04e9acd44f90477ba855c5cfdfa8fde1
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Reaction notes

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