Carbamic acid, N-methyl-, ethyl ester → Butyl methylcarbamate

To a solution of 2-sec butylphenol (1.5 g, 0.01 mole) and ethyl N-methylcarbamate (1.03 g, 0.01 mole) in ethylene dichloride (6 ml) was added phosphoryl chloride (0.77 g, 0.05 mole) and the reaction mixture was refluxed under stirring for twenty hours. It was poured onto ice-cold water. The organic layer separated and aqueous layer was extracted with dichloroethane. The combined organic layer was washed with water, dried (Na2SO4) and distilled to give liquid residue, which was further purified by distillation to give 2-sec butyl N-methylcarbamate of the formula (III) [96% by GLC, DV-101 (3%), 150° C., nitrogen, 30 ml/min.] as a liquid, b.p. 110° C. (vap.)/4 mm; IR: 3320 (N--H), 1730 (--COO--), 1535,1490 and 750 (aromatic); PMR (CDCl3, 90 MHz): 0.81 (3H,t, primary methyl of side chain, 1.58 (2H, m, methylene protons of side chain), 2.88 (4H, doublet overlapping a multiplet, NH--CH3 and benzylic proton), 4.97 (1H, br s, N--H) and 6.95 to 7.25 (4H, m, aromatic).

1. temperaturethe reaction mixture was refluxed
2. additionIt was poured onto ice-cold water
3. customThe organic layer separated
4. extractionaqueous layer was extracted with dichloroethane
5. washThe combined organic layer was washed with water
6. dry with materialdried (Na2SO4)
7. distillationdistilled
8. customto give liquid residue, which
9. distillationwas further purified by distillation

ORD-Eintrag

ord-9880c9027cf94417a87cd63528fcf8be

Quelldatensatz

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05066819