溴乙酸乙酯 → Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylate

HRID 1194

反应方程式

HRID 1194 反应方程式
C(N(CC)CC)C.[NH:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[NH2:9].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1C=CC=CC=1>[CH3:14][C:13]([CH3:16])([O:12][C:10]([NH:8][NH:9][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:11])[CH3:15]

参与物

5

反应物 3

HCID 7748溴乙酸乙酯3 次HCID 8471三乙胺3 次HCID 70091肼基甲酸叔丁酯

产物 1

HCID 13434344Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylate

试剂、催化剂与溶剂 1

HCID 241苯溶剂

实验过程

Triethylamine (13.94 ml., 0.1 mol.) was added to a solution of hydrazine carboxylic acid, 1,1-dimethylethyl ester (13.216 g., 0.1 mole) in benzene (100 ml.), followed by the addition of ethyl bromoacetate (11.09 ml., 0.1 mol.). The reaction mixture was refluxed (oil bath, 95°-100° C.) for 14 hours, after which triethylamine (1.4 ml., 0.01 mol.) was added followed by ethyl bromoacetate (1.1 ml., 0.01 mole). After refluxing for an additional 8 hours, triethylamine (2 ml., 0.015 mol.) and ethyl bromoacetate (1.4 ml., 0.013 mole) were added. The mixture was allowed to reflux for another 14 hours (total 36 hours). After cooling to room temperature, the reaction mixture was filtered and the solid triethylamine, hydrochloride salt was washed with ethyl acetate/hexane (1:1). The combined filtrate was diluted with ethyl acetate, washed with saturated sodium bicarbonate, water, brine, dried (sodium sulfate) and filtered. The filtrate was concentrated in vacuo to afford 19.38 g. of crude product as a yellow syrup which was used for the next reaction without purification.

后处理

  1. temperatureThe reaction mixture was refluxed (oil bath, 95°-100° C.) for 14 hours
  2. temperatureAfter refluxing for an additional 8 hours
  3. temperatureto reflux for another 14 hours (total 36 hours)
  4. filtrationthe reaction mixture was filtered
  5. washthe solid triethylamine, hydrochloride salt was washed with ethyl acetate/hexane (1:1)
  6. additionThe combined filtrate was diluted with ethyl acetate
  7. washwashed with saturated sodium bicarbonate, water, brine
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customto afford 19.38 g
  12. customof crude product as a yellow syrup which was used for the next reaction without purification

来源与证据

ORD记录
ord-d269152a14054777a8d6f6accb67dec8
来源数据集
uspto-grants-1998_03
专利号
US05723457

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