Reaction #5744

ord-88228e4040e04ab3b2c5db9f2b2006b0

Reaction equation

CCOC(=O)C1=C(CSC(=N)N)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1
(-)-S-[(5-cyano-3-carboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridin-2-yl)methyl]isothiourea
Cl.ClCc1ccc[nH+]c1
3-chloromethylpyridinium hydrochloride
[Cl-]
chloride
[K+].[OH-]
KOH
→
CCOC(=O)C1=C(CSCc2cccnc2)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1
(-)-2-(3-pyridinylmethylthio)methyl-5-cyano-3-carboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine

Reactants

CCOC(=O)C1=C(CSC(=N)N)NC(C)=C(C#N)C1c1cccc([N+](=O)[O-])c1
(-)-S-[(5-cyano-3-carboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridin-2-yl)methyl]isothiourea
Cl.ClCc1ccc[nH+]c1
3-chloromethylpyridinium hydrochloride
[Cl-]
chloride
[K+].[OH-]
KOH

Reagents

None

Solvents

c1ccccc1
benzene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto separate a precipitate that
  2. 2
    Filtrationis filtered
  3. 3
    Othertriturated with diethyl ether

Procedure

A mixture of (-)-S-[(5-cyano-3-carboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridin-2-yl)methyl]isothiourea (mg 500), 3-chloromethylpyridinium hydrochloride (mg 190), benzylthriethylammonium chloride (BTEAC mg 80), KOH (4M, ml 2) and benzene (ml 5) is stirred at room temperature for 15 minutes to separate a precipitate that is filtered and triturated with diethyl ether to give mg 450 of (-)-2-(3-pyridinylmethylthio)methyl-5-cyano-3-carboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05245039uspto-grants-1993_09