Hydrogen Sulfide → 2-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Participants

Role	Name	HCID	Charge
Reactant	Hydrogen Sulfide	HCID 402	—
Reactant	Sulfuric Acid	HCID 1118	—
Reactant	Sodium ethoxide	HCID 2723922	—
Reactant	Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate	HCID 3064723	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	2-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine	HCID 11675833	—

Reaction Conditions

Temperature	-15 °C

Reaction Steps

A stirred ethanolic solution (200 ml) of an alkaline alkoxide, for example sodium ethoxide (20 g), is saturated, at +10° C., with dry hydrogen sulfide, cooled to -15° C., and added with a solution of 2-chloromethyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine (25 g) in DME (70 ml). After one hour, the reaction mixture is warmed to 0° C., acidified with H2SO4 (10% water solution; 100 ml) and diluted with water (1400 ml). The precipitate is filtered off, dried in vacuum, and recrystallized from Et2O to give 23 g of 2-mercaptomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine, m.p. 145°-147° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04999362
Source dataset	uspto-grants-1991_03
ORD ID	ord-3c448e32a23e4d4da5273b36e9f225c6
Source note	uspto-grants-1991_03