Hydrochloric Acid → HCID 23282572, compound

HRID 369887Notes

Reaction equation

HRID 369887 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[C:13](N(C)C)=O)[CH:8]=[S:9].BrC[C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>O.C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[CH2:13][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:8]=[S:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 23282608HCID 23282608, compound

Product 1

HCID 23282572HCID 23282572, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (4.92 g) in water (5 ml) is diluted with ethanol (80 ml), and the mixture is subjected to deaeration, and then put under nitrogen atmosphere. To the mixture is added 3-methoxy-4-dimethylaminocarbonylthiobenzaldehyde (20 g), and the mixture is refluxed for 14 hours. After cooling, to the mixture is added dropwise ethyl bromoacetate (9.74 ml), and the mixture is stirred at room temperature for three hours. To the mixture are added ethanol, 1.5N hydrochloric acid and water, and the mixture is extracted with chloroform. The extract is dried over sodium sulfate and concentrated, and the residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=9:1→5.6:1→4:1) to give 3-methoxy-4-ethoxycarbonylmethylthiobenzaldehyde (11.8 g) as white solid.

Workup

  1. temperaturethe mixture is refluxed for 14 hours
  2. temperatureAfter cooling, to the mixture
  3. extractionthe mixture is extracted with chloroform
  4. dry with materialThe extract is dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=9:1→5.6:1→4:1)

Sources & evidence

ORD record
ord-0dee2208f3ca467abec0bf3576769b78
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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