反应详情

A solution of 6-amino-2,3-dichlorobenzyl alcohol (10.0 g., 0.0521 mol) in 250 ml. of boiling benzene was treated with a slow-stream of dry hydrogen chloride for 0.5 hour. The finely divided suspension was cooled slightly, thionyl chloride (12.4 g, 0.104 mol) was added in one portion, and reflux was continued for 2.5 hours. The solution was evaporated in vacuo to remove excess thionyl chloride and hydrogen chloride, and the residue was redissolved in 250 ml. benzene. This solution was added over 1 hour to a reluxing mixture of glycine ethyl ester hydrochloride (29.1 g, 0.208 mol) and triethylamine (31.6 g, 0.313 mol) in 600 ml. CH2Cl2. Reflux was continued for 1 hour, the mixture was allowed to stand overnight and was then extracted with 1N HCl. The extract was washed with CH2Cl2 and ether, made slightly alkaline with concentrated NH4OH and extracted with ether. After drying (K2CO3) and evaporation there remained 8.3 g (58%) of the title product as a light yellow oil which crystallized. The analytical sample was obtained from Skellysolve B as white needles, mp. 60°-61° C.

1. temperatureThe finely divided suspension was cooled slightly
2. temperaturereflux
3. customThe solution was evaporated in vacuo
4. customto remove excess thionyl chloride and hydrogen chloride
5. dissolutionthe residue was redissolved in 250 ml
6. temperatureReflux
7. waitwas continued for 1 hour
8. waitto stand overnight
9. extractionwas then extracted with 1N HCl
10. washThe extract was washed with CH2Cl2 and ether
11. extractionextracted with ether
12. customAfter drying
13. custom(K2CO3) and evaporation there remained 8.3 g (58%) of the title product as a light yellow oil which
14. customcrystallized
15. customThe analytical sample was obtained from Skellysolve B as white needles, mp. 60°-61° C.