Dimethyl Sulfoxide → HCID 87316227, compound

HRID 2045005Notes

Reaction equation

HRID 2045005 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:22][CH2:21][CH2:20][C:19]=2[CH2:23][OH:24])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.CCOCC>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH2:22][CH2:21][CH2:20][C:19]=2[CH:23]=[O:24])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67226847HCID 67226847, compound

Product 1

HCID 87316227HCID 87316227, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (1.1 g) in dichloromethane (30 ml) at −78° C. was added dimethylsulfoxide (6.12 ml). The mixture was stirred at −78° C. for 30 minutes, and then a solution of EXAMPLE 143C (1.2 g) in dichloromethane (10 ml) was added. The mixture was stirred at −78° C. for 2 hours before the addition of triethylamine (10 ml). The mixture was stirred overnight and the temperature was allowed to rise to room temperature. The mixture was diluted with ether (300 ml) and washed with water, brine and dried over Na2SO4. Evaporation of solvent and column purification (5% ethyl acetate in hexane) to give the product.

Workup

  1. stirringThe mixture was stirred overnight
  2. customto rise to room temperature
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvent and column purification (5% ethyl acetate in hexane)
  6. customto give the product

Sources & evidence

ORD record
ord-755d26e19ef9425386097bb5a96141e9
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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