cyclohexyl phenylcarbamate → Cyclohexyl N-cyclohexylcarbamate

HRID 1834152Notes

Reaction equation

HRID 1834152 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>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

3

Reactant 1

HCID 246597cyclohexyl phenylcarbamate

Product 1

HCID 3307288Cyclohexyl N-cyclohexylcarbamateYield 99%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 21.9 g. (0.10 mole) of cyclohexyl carbanilate, 77 ml. of 2-propanol, and 3.0 g. of 5% on carbon was added to a 0.5-1., glass, low pressure, Parr (trademark) shaker bottle. The apparatus was assembled, purged first with nitrogen and then with hydrogen, and pressured with hydrogen to 50 psig. The reaction mixture was agitated at room temperature and 50 to 25 psig for 3.0 hr., followed by an additional 0.8 hr. with little or no gas absorption. The reaction product was filtered through Celite filter aid to remove the catalyst. The solvent was removed in a rotary evaporator under vacuum. The solid residue consisted of 22.3 g. (99% yield) of cyclohexyl cyclohexylcarbamate, m.p. 77°-78°. Anal. Calcd. for C13H23NO2 : C, 69.29; H, 10.30; N, 6.21. Found: C, 69.43; H, 10.10; N, 6.20.

Workup

  1. additionA mixture of 21.9 g
  2. additionof 5% on carbon was added to a 0.5-1
  3. custompurged first with nitrogen
  4. wait, followed by an additional 0.8 hr
  5. customwith little or no gas absorption
  6. filtrationThe reaction product was filtered through Celite
  7. filtrationfilter aid
  8. customto remove the catalyst
  9. customThe solvent was removed in a rotary evaporator under vacuum

Sources & evidence

ORD record
ord-989b36abfb5441678a9181dd36cbece3
Source dataset
uspto-grants-1978_01
Patent number
US04069240

Reaction notes

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