Dimethyl Sulfoxide → HCID 87279454, compound

HRID 1750734Notes

Reaction equation

HRID 1750734 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[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[CH2:24][OH:25])=[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[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[CH:24]=[O:25])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67144985HCID 67144985, compound

Product 1

HCID 87279454HCID 87279454, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (1.1 g, 8.63 mmol) in dichloromethane (30 ml) at −78° C. was added dimethylsulfoxide (6.12 mL, 86 mmol). The mixture was stirred at −78° C. for 30 minutes, and then a solution of Example 8C (1.2 g, 5.75 mmol) in dichloromethane (10 mL) was added. The mixture was stirred at −78° C. for two 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) gave title compound.

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)

Sources & evidence

ORD record
ord-58c849617b804209b2b3efb6a7763686
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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