Hydrazine hydrate (1:1) → alpha-(5-Aminopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile

HRID 1078748노트

반응식

HRID 1078748 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2C(=O)C3C(=CC=CC=3)C2=O)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.NN>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:11]([S:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]#[N:13]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 10673372alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile

생성물 1

HCID 10572107alpha-(5-Aminopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile수율 112.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 4.72 g of α-(3,4-dimethoxyphenyl)-1,3-dihydro-α-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile, 100 mL of ethyl alcohol, and 7.0 mL of hydrazine hydrate is heated under reflux. In about a 30 minutes, a heavy precipitate forms. After 1.33 hours, the reaction is cooled to room temperature and concentrated in vacuo. The residue is warmed on a steam bath with 2N hydrochloric acid for 10 minutes. Diatomaceous silica and chloroform are added, the mixture is shaken thoroughly and then filtered through more diatomaceous silica. The organic phase is washed first with aqueous ammonia, then brine, and, after drying (sodium sulfate), it is concentrated in vacuo to give 3.97 g of the desired product as a yellow oil.

후처리

  1. temperatureis heated
  2. temperatureunder reflux
  3. customIn about a 30 minutes
  4. concentrationconcentrated in vacuo
  5. temperatureThe residue is warmed on a steam bath with 2N hydrochloric acid for 10 minutes
  6. additionDiatomaceous silica and chloroform are added
  7. filtrationfiltered through more diatomaceous silica
  8. washThe organic phase is washed first with aqueous ammonia
  9. dry with materialbrine, and, after drying (sodium sulfate), it
  10. concentrationis concentrated in vacuo

출처 및 근거

ORD 기록
ord-a3e5edb3183943928976bf3dc192a579
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05550149

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