cyclohexyl phenylcarbamate → Cyclohexyl N-cyclohexylcarbamate

HRID 1834153Notes

Reaction equation

HRID 1834153 reaction equation
[C:1](=[O:16])([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Rh].CC(O)C>[CH:3]1([NH:2][C:1](=[O:16])[O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 246597cyclohexyl phenylcarbamate

Product 1

HCID 3307288Cyclohexyl N-cyclohexylcarbamateYield 97%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 21.9 g. (0.10 mole) of cyclohexyl carbanilate, 100 ml. of 2-propanol, and 2.4 g. of 5% Rh on carbon was added to a 300-ml. Magne Drive autoclave. The vessel was sealed, purged first with nitrogen and then with hydrogen, and pressured with hydrogen to 700 psig. The autoclave was agitated at 25° and 500-800 psig for 0.4 hr., followed by an additional 0.9 hr. with little or no gas absorption. The autoclave was cooled and depressurized. The reaction product was removed and filtered through Celite filter aid to remove the catalyst. The solvent was removed in a rotary evaporator under vacuum. The white solid residue consisted of 21.9 g. (97% yield) of cyclohexyl cyclohexylcarbamate, m.p. 77°-78°.

Workup

  1. additionA mixture of 21.9 g
  2. customThe vessel was sealed
  3. custompurged first with nitrogen
  4. wait, followed by an additional 0.9 hr
  5. customwith little or no gas absorption
  6. temperatureThe autoclave was cooled
  7. customThe reaction product was removed
  8. filtrationfiltered through Celite
  9. filtrationfilter aid
  10. customto remove the catalyst
  11. customThe solvent was removed in a rotary evaporator under vacuum

Sources & evidence

ORD record
ord-b32730e07b7b4250b0bdb94f0839a41d
Source dataset
uspto-grants-1978_01
Patent number
US04069240

Reaction notes

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