Thionyl Chloride → HCID 59202189, compound

HRID 1685819Notes

Reaction equation

HRID 1685819 reaction equation
[O:1]=[S:2]1(=[O:22])[CH2:6][CH2:5][CH2:4][CH:3]1[CH:7](O)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1.S(Cl)([Cl:25])=O>O1CCOCC1>[Cl:25][CH:7]([CH:3]1[CH2:4][CH2:5][CH2:6][S:2]1(=[O:22])=[O:1])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59202238HCID 59202238, compound

Product 1

HCID 59202189HCID 59202189, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 2-{4-[(1,1-dioxotetrahydro-1λ6-thiophen-1-yl)hydroxymethyl]phenyl} propionate (400 mg) obtained in Example 38 was dissolved in 1,4-dioxane (5.0 ml), and then to the solution was added thionyl chloride (0.2 ml), and the mixture was stirred at 70° C. overnight. The reaction mixture was quenched with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (420 mg, 99%).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogencarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d5b92902f30d44d5a1bfe406ba18cdfb
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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