Ethyl methyl(phenyl)carbamate → HCID 13119746, compound

HRID 1834154Notes

Reaction equation

HRID 1834154 reaction equation
[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](=[O:7])[O:4][CH2:5][CH3:6]>[Rh].CC(O)C>[CH3:1][N:2]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:3](=[O:7])[O:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 75802Ethyl methyl(phenyl)carbamate

Product 1

HCID 13119746HCID 13119746, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 17.9 g. (0.10 mole) of ethyl N-methylcarbanilate, 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 600 psig. The autoclave was agitated at 30°-40° and 500-800 psig for 0.3 hr., when gas absorption stopped. The reaction product was removed and filtered through Celite filter aid to remove the catalyst. Most of the solvent was removed on a rotary evaporator under vacuum. Distillation gave a quantitative yield of ethyl N-methylcyclohexylcarbamate, b.p. 78°-82° at 2 mm., mostly 81°-2° at 2 mm. An elemental analysis was obtained on a middle cut from the distillation. Anal. Calcd. for C10H19O2N: C, 64.83; H, 10.34; N, 7.56. Found: C, 64.73; H, 10.32; N, 7.44.

Workup

  1. additionA mixture of 17.9 g
  2. customThe vessel was sealed
  3. custompurged first with nitrogen
  4. custom, when gas absorption
  5. customThe reaction product was removed
  6. filtrationfiltered through Celite
  7. filtrationfilter aid
  8. customto remove the catalyst
  9. customMost of the solvent was removed on a rotary evaporator under vacuum
  10. distillationDistillation

Sources & evidence

ORD record
ord-9b19d773dd5546239dfe93e4e3fe541e
Source dataset
uspto-grants-1978_01
Patent number
US04069240

Reaction notes

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