Reaktion #82307

Reaktionsgleichung

1-naphthol

N-methylcarbamothioic acid

sodium

→

1-naphthyl N-methylcarbamate

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 20 hrs
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Waschenwashed with water
4. 4
   Sonstigedried
5. 5
   SonstigeThe removal of solvent
6. 6
   Sonstigeafforded the solid which
7. 7
   Sonstigewas further purified by crystallization

Vorschrift

To a solution of 1-naphthol (1.44 g, 0.01 mole) and S-methyl ester of N-methylcarbamothioic acid (1.575 g, 0.015 mole) in benzene (6 ml) there was added sodium (0.15 g) and the mixture was refluxed for 20 hrs. The reaction mixture was cooled and washed with water and a cold 5% NaOH solution followed by water and brine and then dried. The removal of solvent afforded the solid which was further purified by crystallization to furnish 1-naphthyl N-methylcarbamate of the formula VII, m.p. 140°-141° C., IR: 3305 (N--H), 1715 (--COO--), 1600, 1540, 770 (aromatic): PMR (CdCl3, 90 MHz), 2.86 (3H, d, J=1Hz, NH--CH3, 5.14 (1H, hr. s, N--H) and 7.17 to 8 (7H, m, aromatic).

Quelle