Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 5-(2-Chloroethoxy)-alpha-(3,4-dimethoxyphenyl)-1,3-dihydro-6-methoxy-alpha-[[4-methylphenyl)thio]-2H-isoindole-2-heptanenitrile

HRID 863910Notes

Reaction equation

HRID 863910 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([OH:28])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(C)C=CC(S(O[CH2:49][CH2:50][Cl:51])(=O)=O)=CC=1>>[Cl:51][CH2:50][CH2:49][O:28][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH3:30])[CH2:20][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)([S:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1)[C:12]#[N:13])[CH2:27]2

Participants

3

Reactant 2

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 10530307alpha-(3,4-Dimethoxyphenyl)-1,3-dihydro-5-hydroxy-6-methoxy-alpha-[(4-methylphenyl)thio]-2H-isoindole-2-heptanenitrile

Product 1

HCID 107460535-(2-Chloroethoxy)-alpha-(3,4-dimethoxyphenyl)-1,3-dihydro-6-methoxy-alpha-[[4-methylphenyl)thio]-2H-isoindole-2-heptanenitrileYield 73%

Procedure

The procedure of Example of 32 is used with 0.45 g of α-(3,4-dimethoxyphenyl)-1,3-dihydro-5-hydroxy-6-methoxy-α-[(4-methylphenyl)thio]-2H-isoindole-2-heptanenitrile and 0.65 g of 2-chloroethyl p-toluenesulfonate. This affords 0.367 g of the desired product as a light brown oil. MS(Hi res): m/z Calcd for C33H39N2SClO4 595.2397 Found 595.2391(M+H)

Sources & evidence

ORD record
ord-d9cc5b4607e74691a0093cabc803442b
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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