Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate → 2-(Phenylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

HRID 1493306

Reaction equation

HRID 1493306 reaction equation
Cl[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].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([O-])=O.[Na+].[CH3:38]CO.COCCOC>C(O)C>[C:30]1([S:34][CH2:2][C:3]2[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)[C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:38]=[CH:29][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 3064723Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateHCID 20074477Dimethoxyethane ethanolHCID 23672340Sodium 2-thenoate

Product 1

HCID 198311872-(Phenylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloromethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (5.6 g) in EtOH/DME (5/1; 20 ml) is added dropwise at +10° C. to a stirred solution of sodium thiophenate (1.8 g) in ethanol (10 ml), under N2 atmosphere. After two hours at room temperature the reaction mixture is evaporated under vacuum and the residue is partitioned between Et2O (100 ml) and water (50 ml). The organic phase is washed with a satured solution of sodium bicarbonate (2×20 ml) and water (3×20 ml), dried (Na2SO4) and evaporated to dryness. The residue is recrystallized from isopropylether to give 5.7 g of 2-(phenylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine, m.p. 92°-94° C.

Workup

  1. customAfter two hours at room temperature the reaction mixture is evaporated under vacuum
  2. customthe residue is partitioned between Et2O (100 ml) and water (50 ml)
  3. washThe organic phase is washed with a satured solution of sodium bicarbonate (2×20 ml) and water (3×20 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue is recrystallized from isopropylether

Sources & evidence

ORD record
ord-49b6f32372b04ae5aff401bf11842f9c
Source dataset
uspto-grants-1991_06
Patent number
US05021436

Linked notes

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