Acrylonitrile → 2-[(2-Cyanoethyl)thio]methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

HRID 358992

Reaction equation

HRID 358992 reaction equation
[SH:1][CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:29](#[N:32])[CH:30]=[CH2:31]>CCO.CN(C)C(N(C)C)=N>[C:29]([CH2:30][CH2:31][S:1][CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:32]

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 116758332-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Product 1

HCID 198312032-[(2-Cyanoethyl)thio]methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridineYield 92%

Reagents, catalysts & solvents 2

HCID 664601,1,3,3-TetramethylguanidineCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-mercaptomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1, 4-dihydropyridine (5 g), acrylonitrile (0.66 g) and 1,1,3,3-tetramethylguanidine (0.1 g) in EtOH (60 ml) is stirred at room temperature for 18 hours and then evaporated to dryness. After the usual work-up, the residue is recrystallized from Et2O to give 5.2 g of 2-[(2-cyanoethyl)thio]methyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine m.p. 102°-104° C.

Workup

  1. customevaporated to dryness
  2. customAfter the usual work-up, the residue is recrystallized from Et2O

Sources & evidence

ORD record
ord-c8b960c80a874c2caba73939a516a774
Source dataset
uspto-grants-1991_03
Patent number
US04999362

Linked notes

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