Formaldehyde → HCID 22156957, compound

HRID 1073830Notes

Reaction equation

HRID 1073830 reaction equation
[C:1]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]([CH3:26])[NH:8][C:7]=1[CH2:27][SH:28])([O:3][CH2:4][CH3:5])=[O:2].[CH2:29]=[O:30]>CO>[C:1]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]([CH3:26])[NH:8][C:7]=1[CH2:27][S:28][CH2:29][OH:30])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 116758332-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Product 1

HCID 22156957HCID 22156957, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,5-dicarboethoxy-6-methyl-2-mercaptomethyl-4-(m-nitrophenyl)-1,4-dihydropyridine in MeOH (25 ml) is added with a 37% formaldehyde aqueous solution (6 ml, 79 mmol.). The obtained solution is refluxed for 1.5 hours. The solvent is evaporated under reduced pressure and the residue is dissolved in ethyl acetate (50 ml). The organic phase is washed (3×60 ml), separated, dried on Na2SD4, filtered and the solvent is evaporated under reduced pressure; the oily residue is crystallized from isopropyl ether, obtaining 3 g of 3,5-dicarboethoxy-4-(m-nitro-phenyl)-6-methyl-2-(hydroxymethylthiomethyl)-1,4-dihydropyridine, m.p. 113°-114° C.

Workup

  1. temperatureThe obtained solution is refluxed for 1.5 hours
  2. customThe solvent is evaporated under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate (50 ml)
  4. washThe organic phase is washed (3×60 ml)
  5. customseparated
  6. customdried on Na2SD4
  7. filtrationfiltered
  8. customthe solvent is evaporated under reduced pressure
  9. customthe oily residue is crystallized from isopropyl ether

Sources & evidence

ORD record
ord-35c13d0229eb4e36b053c72b07cd2dd2
Source dataset
uspto-grants-1990_11
Patent number
US04971984

Reaction notes

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