反应详情

4-(2-Pyrrolidin-1-ylethoxy)aniline (17.3 g.) in ethanol (20 ml.) is added dropwise to a mixture of ethanol (55 ml.), carbon disulphide (10 ml.) and aqueous ammonia (density = 0.88, 20 ml.) at 0°C. After 2 hours the solid is collected and washed with acetone, m.p. 143° - 150°C. (dec.). This solid (23.6 g.), chloroform (114 ml.) and triethylamine (11.9 ml.) are stirred, and ethyl chloroformate (8.6 ml.) added with cooling so that the temperature remains below 0°C. After stirring for 30 minutes below 0°C. and 1 hour at 20°C., excess of 10% sodium hydroxide is added. The chloroform is separated, washed with water, dried and evaporated. The residue is dissolved in benzene and the solution filtered through alumina. The filtrate is evaporated and the residue distilled to give 4-(2-pyrrolidin-1-ylethoxy)phenyl isothiocyanate, b.p. 160° - 168°C./0.2 mm.

1. customAfter 2 hours the solid is collected
2. washwashed with acetone, m.p. 143° - 150°C. (dec.)
3. additionethyl chloroformate (8.6 ml.) added
4. temperaturewith cooling so that the temperature
5. customremains below 0°C
6. stirringAfter stirring for 30 minutes below 0°C. and 1 hour at 20°C., excess of 10% sodium hydroxide
7. additionis added
8. customThe chloroform is separated
9. washwashed with water
10. customdried
11. customevaporated
12. dissolutionThe residue is dissolved in benzene
13. filtrationthe solution filtered through alumina
14. customThe filtrate is evaporated
15. distillationthe residue distilled