4-Aminobenzoic Acid → HCID 23046218, compound

HRID 2107632Notes

Reaction equation

HRID 2107632 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[SH:16][CH2:17][C:18]1[NH:19][C:20]([CH3:43])=[C:21]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=2)[C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[NH2:44][C:45]1[CH:53]=[CH:52][C:48]([C:49](O)=[O:50])=[CH:47][CH:46]=1>O1CCCC1>[NH2:44][C:45]1[CH:53]=[CH:52][C:48]([C:49]([S:16][CH2:17][C:18]2[NH:19][C:20]([CH3:43])=[C:21]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=3)[C:23]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:50])=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 116758332-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Product 1

HCID 23046218HCID 23046218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of dicyclohexylcarbodiimide (g 1.5) in tetrahydrofuran is added dropwise to a solution of 2-mercaptomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (g 2.7) and p-aminobenzoic acid (g 1.0) in tetrahydrofuran (20 ml) cooled to 0° C. in nitrogen atmosphere, the mixture is stirred at 0° C. for 15 minutes and then warmed to room temperature for 18 hours. The precipitate formed is filtered and the solvent is evaporated in vacuum. The residue is dissolved in ethyl acetate (150 ml) and washed with water (3×40 ml), with a sodium bicarbonate solution (3×30 ml) and then once again with water (3×20 ml). After drying on sodium sulphate and evaporation in vacuum of the solvent, the residue is purified by chromatography on silica gel (g 100) eluting with petroleum ether/ethyl acetate (8/2). The product is recrystallized from isopropyl ether. 3,2 g of 2-(p-aminobenzoylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine are obtained; m.p. 78°-80° C.

Workup

  1. temperaturewarmed to room temperature for 18 hours
  2. customThe precipitate formed
  3. filtrationis filtered
  4. customthe solvent is evaporated in vacuum
  5. dissolutionThe residue is dissolved in ethyl acetate (150 ml)
  6. washwashed with water (3×40 ml), with a sodium bicarbonate solution (3×30 ml)
  7. customAfter drying on sodium sulphate and evaporation in vacuum of the solvent
  8. customthe residue is purified by chromatography on silica gel (g 100)
  9. washeluting with petroleum ether/ethyl acetate (8/2)
  10. customThe product is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-35a11ba3ad0043fa9a0fea995c5e21a8
Source dataset
uspto-grants-1990_06
Patent number
US04935433

Reaction notes

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