Ethyl cyanoacetate → HCID 15219945、化合物

HRID 1974434ノート

反応式

HRID 1974434 の反応式
[NH:1]([CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([CH2:19][C:20](OCC)=[O:21])#[N:18].C([O-])(=O)C.[NH4+]>>[C:17]([C:19]1[C:20](=[O:21])[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:8][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)#[N:18]

参加物

4

反応物 3

HCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 11326242-anilinoacetophenone

生成物 1

HCID 15219945HCID 15219945、化合物収率 35%

反応条件

温度
180 °C

実験手順

A mixture of 21.1 grams (0.1 mol) of 2-anilinoacetophenone, 31.8 grams (0.28 mol) of ethyl cyanoacetate, and 8 grams (0.13 mol) of ammonium acetate were placed in a reaction flask fitted with a distillation head. The reaction mixture was placed in an oil bath pre-heated to a temperature of 180° C. At a reaction temperature of 100° C. the solid mixture liquified and stirred easily. The internal temperature of the reaction rose to 150° C. over a period of 30 minutes while a colorless distillate was removed. After 30 minutes no further distillate was collected and the product mixture was cooled. To the dark homogeneous liquid product was added 40 mL of absolute ethanol with stirring. The precipitated yellow crystalline product was collected by filtration and washed with 3×10 mL ethanol, 2×25 mL ligroin, and air dried to afford 10.05 grams of crude product. Recrystallization from 80 mL of acetonitrile gave 9.1 grams (35 mmol, 35 % yield) of 3-cyano -1,4-diphenyl-3-pyrrolin-2-one as yellow crystals, m. p.=188°-190° C. Elemental Analysis: Calculated: C=78.44, H=4.65, N=10.76; Found: C=78.36, H=4.90, N=10.81.

後処理

  1. customwere placed in a reaction flask
  2. customfitted with a distillation head
  3. customThe reaction mixture was placed in an oil bath
  4. customAt a reaction temperature of 100° C.
  5. customwas removed
  6. distillationAfter 30 minutes no further distillate was collected
  7. temperaturethe product mixture was cooled
  8. additionTo the dark homogeneous liquid product was added 40 mL of absolute ethanol
  9. stirringwith stirring
  10. filtrationThe precipitated yellow crystalline product was collected by filtration
  11. washwashed with 3×10 mL ethanol, 2×25 mL ligroin, and air
  12. customdried
  13. customto afford 10.05 grams of crude product
  14. customRecrystallization from 80 mL of acetonitrile

出典と根拠

ORDレコード
ord-8b94df35da7d452faffbdbcbb5a0a95d
出典データセット
uspto-grants-1994_02
特許番号
US05283165

反応ノート

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