Triethylamine → HCID 9821872, compound

HRID 1534636Notes

Reaction equation

HRID 1534636 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:7]([C:13]([OH:15])=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4].C(N(CC)CC)C.[CH3:32][S:33][CH2:34]Cl>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:7]([C:13]([O:15][CH2:34][S:33][CH3:32])=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16916Chloromethyl methyl sulfideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

Product 1

HCID 9821872HCID 9821872, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydro pyridine-3,5-dicarboxylic acid 5-methyl ester(3.32g), triethylamine(2.5ml)and chloromethyl methyl sulfide(0.9ml) in 30ml of acetonitrile was heated at 65° C. for 3 hours. The solvent was removed in vacuum, and then the residue was dissolved in ethylacetate. The ethylacetate solution was washed with water and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The oily residue was purified by silica gel column chromatography (ethylacetate:n-hexane=1:3). The eluent was concentrated in vacuum to afford a yellow solid which was recrystallized from methyl alcohol to give the titled compound(1.2g):

Workup

  1. customThe solvent was removed in vacuum
  2. dissolutionthe residue was dissolved in ethylacetate
  3. washThe ethylacetate solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe oily residue was purified by silica gel column chromatography (ethylacetate:n-hexane=1:3)
  7. concentrationThe eluent was concentrated in vacuum
  8. customto afford a yellow solid which
  9. customwas recrystallized from methyl alcohol

Sources & evidence

ORD record
ord-9a09385ec8474c8d9a9adc90997a5746
Source dataset
uspto-grants-1992_02
Patent number
US05089624

Reaction notes

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