Dimethyl Sulfoxide → HCID 15480788, compound

HRID 842947Notes

Reaction equation

HRID 842947 reaction equation
[C:1]([C:3]1([C:14]2[C:23]3[O:22][CH2:21][CH2:20][O:19][C:18]=3[C:17]([O:24][CH3:25])=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH:5](C(OC)=O)[CH2:4]1)#[N:2].CS(C)=O.[Cl-].[Na+]>O>[C:1]([C:3]1([C:14]2[C:23]3[O:22][CH2:21][CH2:20][O:19][C:18]=3[C:17]([O:24][CH3:25])=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 15480787HCID 15480787, compound

Product 1

HCID 15480788HCID 15480788, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

A mixture of Compound 1c (5.0 g, 15 mmol) obtained in Step C, DMSO(50 mL), water (5 mL), and sodium chloride (5.0 g) was stirred at 150° C. for 5 hours. The mixture was allowed to cool, and added water, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=3/1) to give Compound 1 (3.6 g, 86%) as a white solid.

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-301838e204e54b50b964c98bfd95dcf3
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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