Chloroacetyl chloride → 2-chloro-N-(2-methoxyethyl)acetamide

温度

0 °C

In a three-necked 2L round bottom flask fitted with two 500 mL addition funnels, containing 56.4g (39.8 mL, 0.50 mole) chloroacetyl chloride in 400 mL dichloromethane and 20g (0.50 mole) sodium hydroxide in 400 mL water, respectively, and a water-cooled condenser, was placed 35.7g (41.3 mL, 0.48 mole) 2-methoxyethylamine, 100 mL water, 100 mL dichloro-methane. The reaction vessel was cooled to 0° C. by a salt-ice bath. The organic and aqueous solutions were allowed to add slowly, ~0.25 mL per minute, to the reaction mixture. During the addition the pH of the water phase of the reaction was monitored and the rate of addition of the alkali solution adjusted so as to maintain pH=12. When the addition was complete, the mixture was allowed to warm to room temperature and stir overnight. The organic layer was removed by siphon and dried with magnesium sulfate for four hours. The mixture was filtered through #4 filter paper on a large Buchner funnel and the sulfate washed with 2×100 mL fresh dichloromethane. The combined filtrates were then placed in 2L round bottomed flask and the mixture distilled at 1 torr. Fractions collected from 55° C. to 60° C. were combined and analyzed by NMR. Yield 31.1g (43% based on starting 2-methoxyethylamine). TLC (silica on glass, 2% methanol in dichloromethane) Rf =0.40. 1H(δ,CDC13) 3.28(s,3H), 3.40(m,4H), 3.97(s,2H), 6.92(br, 1H). 13C{1H} (δ, CDCl3) 39.27, 42.32, 58.60, 70.54, 166.22.

1. additionto add slowly
2. additionthe rate of addition of the alkali solution
3. temperatureto maintain pH=12
4. additionWhen the addition
5. temperatureto warm to room temperature
6. customThe organic layer was removed by siphon
7. dry with materialdried with magnesium sulfate for four hours
8. filtrationThe mixture was filtered through #4
9. filtrationfilter paper on a large Buchner funnel
10. washthe sulfate washed with 2×100 mL fresh dichloromethane
11. distillationthe mixture distilled at 1 torr
12. customFractions collected from 55° C. to 60° C.

ORDレコード

ord-7746b720bdbd4fafb0e7e5e272faee43

出典データセット

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05290537