Dimethyl Sulfoxide → HCID 20770558, compound

HRID 1813890Notes

Reaction equation

HRID 1813890 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](=S)=[S:16].[H-].[Na+].IC.[CH3:22][S:23]([CH3:25])=O>>[CH3:14][O:13][C:11](=[O:12])[C:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])=[C:22]([S:16][CH3:15])[S:23][CH3:25]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 555619Methyl phenylsulfonyl acetate

Product 1

HCID 20770558HCID 20770558, compound

Procedure

Methyl phenylsulfonylacetate (5 g, 23.3 mmol) was mixed with carbon disulfide (1.77 g, 23.3 mmol) in anhydrous DMSO (100 ml) at room temperature. Sodium hydride (60% in mineral oil, 1.2 g, 48.9 mmol) was added portionwise. After stirring at room temperature for 1 hour, iodomethane (6.9 g, 48.9 mmol) was added neat and the reaction mixture was stirred overnight. The reaction mixture was quenched by the addition of water, and the resulting mixture extracted with dichloromethane. The organic layer was purified via flash chromatography and concentrated in vacuo to provide crude 2-benzenesulfonyl-3,3-bis-methylsulfanyl-acrylic acid methyl ester, which was further purified by recrystallization from methanol to yield 3.7 grams of white solid. 1H NMR (500 MHz, CDCl3): δ 8.1 (d, 2H), 7.6 (t, 1H), 7.5 (t, 2H), 3.9 (s, 3H), 2.4 (s, 3H), 2.2 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionthe resulting mixture extracted with dichloromethane
  4. customThe organic layer was purified via flash chromatography
  5. concentrationconcentrated in vacuo
  6. customto provide crude 2-benzenesulfonyl-3,3-bis-methylsulfanyl-acrylic acid methyl ester, which
  7. customwas further purified by recrystallization from methanol

Sources & evidence

ORD record
ord-cf6d44ebb7c34889bd0cbca389bcdcdc
Source dataset
uspto-grants-2005_04
Patent number
US06875771B2

Reaction notes

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