Phthalimide → a-(Cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-1,3-dioxo-2H-isoindole-2-heptanenitrile

HRID 863902Notes

Reaction equation

HRID 863902 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]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].[K].[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>>[CH:21]1([S:20][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=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])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 6809PhthalimideHCID 5462222PotassiumHCID 11795020alpha-(5-Chloropentyl)-alpha-(cyclohexylthio)-3,4-dimethoxy-benzeneacetonitrile

Product 1

HCID 10505769a-(Cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-1,3-dioxo-2H-isoindole-2-heptanenitrile

Procedure

The procedure of Example 24 is repeated using 2.1 g of α-(5-chloropentyl)-α-(cyclohexylthio)-3,4-dimethoxybenzeneacetonitrile and 0.954 g of the potassium salt of phthalimide. This affords 2.13 g of the desired product as a colorless oil. Calcd for C29H34N2SO4 : C=68.75, H=6.76, N=5.53, S=6.33 Found C=68.49, H=6.84, N=5.35, S=5.98

Sources & evidence

ORD record
ord-be8062b66edb4a358dd01ea9d2ac6d28
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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