Ethyl Acetate → HCID 68742153, compound

HRID 2378567Notes

Reaction equation

HRID 2378567 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:11][C:10]=2[N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1.[C:23](OCC)(=O)C.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>CO.C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([O:19][CH3:23])=[O:18])=[CH:11][C:10]=2[N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 28016283-{4-[(4-Methylphenyl)sulfanyl]-3-nitrophenyl}prop-2-enoic acid

Product 1

HCID 68742153HCID 68742153, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-(4-methylphenylthio)-3-nitrophenyl]acrylic acid (631 mg, MAYB) in a mixture of methanol (12.6 ml), ethyl acetate (6.3 ml) and THF (6.3 ml) was added dropwise to methanol (12.6 ml) beforehand under ice cooling, and then the mixture was added with a solution of thionyl chloride (735 μl, KANTO) in methanol (50 ml) under ice cooling, stirred for 30 minutes, then warmed to room temperature, and further stirred for 15.5 hours. The reaction mixture was poured into aqueous sodium hydrogencarbonate (50 ml) for neutralization, and extracted with ethyl acetate (50 ml), and the organic layer was washed with saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate s-1, 659 mg).

Workup

  1. stirringfurther stirred for 15.5 hours
  2. extractionextracted with ethyl acetate (50 ml)
  3. washthe organic layer was washed with saturated brine
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c231e4532c254a35996e031522167350
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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