alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile → alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile

HRID 863875노트

반응식

HRID 863875 반응식
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>CN(C)C=O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:7]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]2[C:28](=[O:38])[C:29]3[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31]2=[O:33])[C:8]#[N:9])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

참가 물질

4

반응물 2

HCID 19042083alpha-(5-Iodopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileHCID 24194345Phthalimide potassium salt

생성물 1

HCID 10673372alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile수율 77.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 6.12 g of α-(5-iodopentyl)-3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile and 2.22 g of potassium phthalimide and 50 mL of N,N-dimethylformamide is heated on a steam bath for 2 hours. The reaction solution is concentrated in vacuo and the residue is distributed between diethyl etherwater, with agitation. The organic layer is washed with 1N sodium hydroxide, followed by aqueous potassium bicarbonate. The solution is dried (sodium sulfate), and the volatiles removee in vacuo. Chromatography on silica gel, with gradient elution progressing from hexane to chloroform to methyl alcohol, affords 4.77 g of the desired product as a fluorescent oil. MS(FAB): m/z 515(M+H), 391(M-TolSH). Calcd for C30H30N2O4S 3/8H2O: C=69.11, H=5.95, N=5.37, S=6.14 Found C=69.34, H=5.78, N=5.23, S=5.79

후처리

  1. temperatureis heated on a steam bath for 2 hours
  2. concentrationThe reaction solution is concentrated in vacuo
  3. washThe organic layer is washed with 1N sodium hydroxide
  4. dry with materialThe solution is dried (sodium sulfate)

출처 및 근거

ORD 기록
ord-d005303e8b214214bccee0a8f7902288
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05561141

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