Pyrrole-2-Carboxylic Acid → beta-Oxo-alpha-(phenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

HRID 236353

반응식

HRID 236353 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].CC(C)([O-])C.[K+].[NH:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](O)=[O:25].P(C#N)(=O)(OCC)OCC>CN(C)C=O.O>[O:25]=[C:24]([C:20]1[NH:19][CH:23]=[CH:22][CH:21]=1)[CH:3]([C:4](=[O:5])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2]

참가 물질

7

반응물 4

HCID 12473Pyrrole-2-Carboxylic AcidHCID 69296Acetamide, 2-cyano-N-phenyl-HCID 76257Diethyl cyanophosphonateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 13370089beta-Oxo-alpha-(phenylcarbamoyl)-beta-(2-pyrrolyl)-propionitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

to a solution of 1.6 g of α-cyanoacetanilide in 10 ml of dimethylformamide is added 3.4 g of potassium t-butoxide. The stirred cooled suspension is treated with a solution of 1.1 g of pyrrole-2-carboxylic acid and 1.4 ml of diethyl phosphorocyanidate in 6 ml of dimethylformamide. After standing for one half hour, solution is treated with 80 ml of cold water, filtered and acidified with 6N hydrochloric acid. The suspended product is collected, washed with water, dried, and dissolved in ethyl acetate. The ethyl acetate solution is filtered and evaporated to dryness. Recrystallization from ether-ethanol yields β-oxo-α-(phenylcarbamoyl)-β-(2-pyrrolyl)-propionitrile of Example 1.

후처리

  1. temperatureThe stirred cooled suspension
  2. waitAfter standing for one half hour
  3. filtrationfiltered
  4. customThe suspended product is collected
  5. washwashed with water
  6. customdried
  7. dissolutiondissolved in ethyl acetate
  8. filtrationThe ethyl acetate solution is filtered
  9. customevaporated to dryness
  10. customRecrystallization from ether-ethanol

출처 및 근거

ORD 기록
ord-b292133de2964c528d6c4406c7bce408
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644010

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