Water → HCID 86587496, compound

HRID 987463Notes

Reaction equation

HRID 987463 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[NH:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:30]2)=CC=1.O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:7](=[S:30])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 2992343HCID 2992343, compound

Product 1

HCID 86587496HCID 86587496, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 3,4,5-trimethoxyoxanilate (3.0 g) was dissolved in benzene (20 mL), and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (2.14 g) was added to the solution. The reaction mixture was stirred at 80° C. for 1 hour, and water was added thereto. After conducting extraction with ethyl acetate, the resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound.

Workup

  1. extractionextraction with ethyl acetate
  2. washthe resultant organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-e78ab0fb7f5e4845af27768e18e4984a
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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