Ethyl bromoacetate → Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylate

HRID 1194

反応式

HRID 1194 の反応式
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]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetate3 回HCID 8471Triethylamine3 回HCID 70091tert-Butyl carbazate

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d269152a14054777a8d6f6accb67dec8
出典データセット
uspto-grants-1998_03
特許番号
US05723457

関連ノート

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