Hydrochloric Acid → 1-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane

HRID 342040

反応式

HRID 342040 の反応式
[C-:1]#[N:2].[K+].[CH2:4]([NH2:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:12]([C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1)=O.Cl>O.C(O)C>[CH2:4]([NH:11][CH:12]([C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1)[C:1]#[N:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 9032Potassium CyanideHCID 9964122Ethyl 1-formylcyclopropanecarboxylate

生成物 1

HCID 153910461-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane収率 87.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

An eggplant type flask was charged with 131 mg of potassium cyanide and 539 mg of benzylamine, and the contents were dispersed in 1 ml of water. Thereto was added dropwise 146 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2 ml of ethanol at room temperature, followed by dropwise addition of 0.2 ml of concentrated hydrochloric acid. The reaction solution was stirred for 2.5 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and, after removing insoluble matter by filtration, concentrated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 231 mg (87%) of the title compound in the form of colorless oil.

後処理

  1. customcompletion of the reaction
  2. extractionextracted with ethyl acetate
  3. washNext, the resulting organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter removing insoluble matter
  6. filtrationby filtration
  7. concentrationconcentrated under a reduced pressure

出典と根拠

ORDレコード
ord-d89e0989ae9549d7814e916ed2e809d7
出典データセット
uspto-grants-1999_01
特許番号
US05856518

関連ノート

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