Hydrochloric Acid → 1-Methyl-5-(p-toluoyl)pyrrole-2-acetonitrile

HRID 848042

반응식

HRID 848042 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](C#N)=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]#[N:20].ClC(Cl)(Cl)C(O)=O.Cl>CCOCC.C(Cl)Cl>[CH3:12][N:13]1[C:17]([C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]#[N:20]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6421Trichloroacetic AcidHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 641326Oxo-P-tolyl-acetonitrile

생성물 1

HCID 111074051-Methyl-5-(p-toluoyl)pyrrole-2-acetonitrile수율 30%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A solution of 0.16 g (1.1 mmole) of 4-methylbenzoylcyanide, 0.13 g (1.1 mmole) of 1-methylpyrrole-2-acetonitrile and 4 mg of trichloroacetic acid in 0.4 ml of ether was allowed to stand in the dark under nitrogen at 25°. After three days, a small amount of hydrogen chloride gas was admitted to the vessel. The mixture was allowed to stand for 14 days. It was diluted with methylene chloride and the solution washed with sodium hydroxide. The solution was dried (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed on 37 ml of silica gel. The fractions eluted with a mixture of 1,1,1-trichloroethane:hexane, 1:1 were discarded. The fractions eluted with 1,1,1-trichloroethaneihexane 3:1 were collected. The solvent was evaporated to give 0.80 g of dark solid 1-methyl-5-(4-methylbenzoyl)pyrrole-2-acetonitrile (30 percent yield). It was recrystallized from 1,1,1-trichloroethaneihexane to give brown solid, mp 103°-104°, undepressed by admixture with authentic material.

후처리

  1. customat 25°
  2. waitto stand for 14 days
  3. washthe solution washed with sodium hydroxide
  4. dry with materialThe solution was dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was chromatographed on 37 ml of silica gel
  7. washThe fractions eluted with a mixture of 1,1,1-trichloroethane
  8. washThe fractions eluted with 1,1,1-trichloroethaneihexane 3:1
  9. customwere collected
  10. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-d262c5a48a2b48c5ba7c3c67bf66185a
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04294760

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