Dimethyl Sulfoxide → HCID 59367724, compound

HRID 1643480Notes

Reaction equation

HRID 1643480 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([S:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[CH2:29][OH:30])(=[O:22])=[O:21])=[C:15]([CH3:31])[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH3:31])[C:16]([S:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[CH:29]=[O:30])(=[O:21])=[O:22])=[C:17]([CH3:19])[CH:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 43574491[1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-yl]-methanol

Product 1

HCID 59367724HCID 59367724, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

DMSO (12.76 mmol, 4 eq.) was dissolved in methylene chloride (10 ml), oxalyl chloride (6.38 mmol, 2 eq) was added under nitrogen at −78° C. and the mixture was then stirred at this temperature for 30 min. (1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol (3.1 mmol, 1 eq) was dissolved in methylene chloride (10 ml), the solution was added dropwise to the reaction solution at −78° C. and this was then stirred for 30 min. Triethylamine (12.76 mmol, 5 eq) was added and the reaction solution was warmed to room temperature and stirred for 1 h. Water (20 ml) was added to the reaction mixture and the mixture was extracted with methylene chloride (3×60 ml). The organic phase was dried over sodium sulfate and filtered and the filtrate was concentrated to dryness under reduced pressure. The crude product was employed in the next stage without further purification. Yield: 90%

Workup

  1. additionthe solution was added dropwise to the reaction solution at −78° C.
  2. stirringstirred for 1 h
  3. extractionthe mixture was extracted with methylene chloride (3×60 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to dryness under reduced pressure
  7. customThe crude product was employed in the next stage without further purification

Sources & evidence

ORD record
ord-c7a42e0a88b64232a84b051b8236773c
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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