Water → HCID 14722815, compound

HRID 477902Notes

Reaction equation

HRID 477902 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12](=O)[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.[C:24]([O-:27])(=O)C.[NH4+:28].[OH2:29].[C:30]1([CH3:36])C=CC=[CH:32][CH:31]=1>>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]1[C:31]([C:32]([O:27][CH3:24])=[O:29])=[C:30]([CH3:36])[NH:28][C:12]([CH3:13])=[C:11]1[S:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 69962-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 13794947HCID 13794947, compound

Product 1

HCID 14722815HCID 14722815, compound

Procedure

A solution of 4-hydroxyphenylsulfonylacetone (5.7 g), 2-chlorobenzaldehyde (3.7 g), and ammonium acetate (50 mg) in toluene (50 ml) was heated at reflux using a Dean-Stark water separator for 2 hours. About 20 ml of the solvent was removed on a rotary evaporator. Methyl β-aminocrotonate (3.1 g) and methanol (40 ml) were then added to the remaining toluene solution. The resulting mixture was heated under nitrogen for 18 hours. The cooled reaction mixture was evaporated to dryness, and the residue was chromatographed on silica gel (elution with 1:3 to 1:2 ethyl acetate/hexane) to yield 4-(2-chlorophenyl)-3-(4-hydroxyphenyl)sulfonyl-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine, m.p. 223°-225° C.

Workup

  1. temperatureat reflux
  2. customAbout 20 ml of the solvent was removed on a rotary evaporator
  3. additionMethyl β-aminocrotonate (3.1 g) and methanol (40 ml) were then added to the remaining toluene solution
  4. temperatureThe resulting mixture was heated under nitrogen for 18 hours
  5. customThe cooled reaction mixture
  6. customwas evaporated to dryness
  7. customthe residue was chromatographed on silica gel (elution with 1:3 to 1:2 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-892db6d2e95340a4b9a6f41f0afeb21b
Source dataset
uspto-grants-1989_12
Patent number
US04889866

Reaction notes

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