1H-Pyrrole-2-acetonitrile, 1-methyl- → 5-(rho-Isopropylbenzoyl)-1-methylpyrrole-2-acetonitrile

HRID 863641

반응식

HRID 863641 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[CH3:17][N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]#[N:25]>ClCCCl>[CH:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([C:22]2[N:18]([CH3:17])[C:19]([CH2:23][C:24]#[N:25])=[CH:20][CH:21]=2)=[O:13])=[CH:10][CH:9]=1)([CH3:7])[CH3:6]

참가 물질

5

반응물 3

HCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 27594864-Isopropylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 184243265-(rho-Isopropylbenzoyl)-1-methylpyrrole-2-acetonitrile

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

To a suspension of 17.5 g. (0.131 mole) aluminum chloride in 60 ml. 1,2-dichloroethane is added 24 g. (0.131 mole) ρ-isopropylbenzoyl chloride. The resulting mixture is added slowly and dropwise to a chilled solution (0° C.) of 15.7 g. (0.131 mole) 1-methylpyrrole-2-acetonitrile in 100 ml. of 1,2-dichloroethane. After addition is complete, the mixture is stirred at room temperature for twenty minutes and heated at reflux for three minutes. The reaction mixture is then cooled and poured into ice-dilute hydrochloric acid. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid and a saturated solution of sodium chloride; dried over magnesium sulfate; and the solvent evaporated. The product, 5-(ρ-isopropylbenzoyl)-1-methylpyrrole-2-acetonitrile, is isolated from the residual oil by column chromatography. The column is packed with acid washed alumina and eluted with benzene, ether and ethylacetate. The product is found in the first compound-bearing fraction which absorbs ultraviolet light at approximately 250 m. It is purified by recrystallization twice in ether:pentane (9 g.; 20% yield), M.P. 59°-64° C.

후처리

  1. additionTo a suspension of 17.5 g
  2. additionThe resulting mixture is added slowly and dropwise to a chilled solution (0° C.) of 15.7 g
  3. additionAfter addition
  4. temperatureheated
  5. temperatureat reflux for three minutes
  6. temperatureThe reaction mixture is then cooled
  7. additionpoured into ice-dilute hydrochloric acid
  8. customThe organic phase is separated
  9. washwashed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid
  10. dry with materialdried over magnesium sulfate
  11. customand the solvent evaporated

출처 및 근거

ORD 기록
ord-b312f5bcd66b48b5bb1e544de149dd77
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721347

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