Ethyl chloroacetate → 2-Benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one

HRID 21408

반응식

HRID 21408 반응식
[H-].[Na+].[CH:3](=[N:10][N:11]=[C:12]1[NH:16][C:15](=[O:17])[CH2:14][N:13]1[CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O.C(Cl)(Cl)Cl.O>[CH:3](=[N:10][N:11]=[C:12]1[N:16]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:15](=[O:17])[CH2:14][N:13]1[CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 1360406052-Benzylidenehydrazono-1-methoxycarbonylmethylimidazolidin-4-one

생성물 1

HCID 541207212-Benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one수율 44.4%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6212Chloroform용매2회HCID 6228Dimethylformamide용매2회

반응 조건

온도
30 °C

실험 절차

In 20 ml of dimethylformamide (DMF) was suspended 96 mg of 60% sodium hydride under ice-cooling, 5 ml of a DMF solution of 548 mg of 2-benzylidenehydrazono-1-methoxycarbonylmethylimidazolidin-4-one was gradually added to the suspension. After stirring the mixture for one hour at 30° C., 254 mg of ethyl chloroacetate was gradually added dropwise thereto, followed by stirring for one hour at 80° C. After cooling the reaction mixture, water and chloroform was added thereto to distribute the mixture between water and chloroform, and the aqueous layer was further extracted three times with chloroform. The organic layer was combined with the extract, the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue formed was recrystallized from a mixture of chloroform and n-hexane to obtain 320 mg of 2-benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one.

후처리

  1. temperaturecooling
  2. stirringby stirring for one hour at 80° C
  3. additionwas added
  4. extractionthe aqueous layer was further extracted three times with chloroform
  5. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue formed
  8. customwas recrystallized from a mixture of chloroform and n-hexane

출처 및 근거

ORD 기록
ord-95f5bb33bf7440c88b09193ba4fb2a51
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05422360

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