Methyl phenylcarbamate → Methyl cyclohexylcarbamate

A mixture of 15.1 g. (0.10 mole) of methyl carbanilate, 105 ml. of 2-propanol, and 0.60 g. of 5% Rh on carbon was added to a 300-ml. Magne Drive (tradmark) autoclave. The vessel was sealed, purged first with nitrogen and then with hydrogen, and pressured with hydrogen to 600 psig. The autoclave was heated with agitation at 500-800 psig for 0.3 hr. at 25°-75°, followed by an additional 0.8 hr. at 75° with little or no gas absorption. The autoclave was cooled and depressurized. The reaction product was removed and filtered through Celite (trademark) filter aid to remove the catalyst. The solvent was removed in a rotary evaporator under vacuum. The white solid residue was dried in a vacuum dessicator and consisted of 15.1 g. (96% yield) of methyl cyclohexylcarbamate, m.p. 73°-74°. An authentic sample prepared from cyclohexyl isocyanate and methanol melted at 73.5°-74°.

1. additionA mixture of 15.1 g
2. customThe vessel was sealed
3. custompurged first with nitrogen
4. temperatureThe autoclave was heated with agitation at 500-800 psig for 0.3 hr
5. customat 75° with little or no gas absorption
6. temperatureThe autoclave was cooled
7. customThe reaction product was removed
8. filtrationfiltered through Celite (trademark)
9. filtrationfilter aid
10. customto remove the catalyst
11. customThe solvent was removed in a rotary evaporator under vacuum
12. customThe white solid residue was dried in a vacuum dessicator

ORD record

ord-cbcb39f6cc99441aaefa95c77ed3eab3

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04069240