Dimethyl Sulfoxide → HCID 10262220, compound

HRID 2120870Notes

Reaction equation

HRID 2120870 reaction equation
ClCCl.C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:14][C:15]1[C:19]([CH:20]([OH:22])[CH3:21])=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:17][N:16]=1>[Cl-].[Na+].O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:14][C:15]1[C:19]([C:20](=[O:22])[CH3:21])=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:17][N:16]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 23435638HCID 23435638, compound

Product 1

HCID 10262220HCID 10262220, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

To a dichloromethane solution of oxalyl chloride was added DMSO at −78° C., the mixture was stirred at −78° C. for 15 min and followed by addition of a dichloromethane solution of compound the above Compound 26. The reaction mixture was stirred for 30 min at −78° C., then triethylamine was added, after which the reaction mixture was allowed to warm to room temperature gradually. To the reaction mixture was added ethyl acetate and brine. The organic phase was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product, obtained in 94% yield, was used directly for the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred for 30 min at −78° C.
  2. temperatureto warm to room temperature gradually
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cb5c81f3b0724a52b32367de62573274
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

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