Dimethyl Sulfoxide → HCID 87279390, compound

HRID 624338Notes

Reaction equation

HRID 624338 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][C:22]([CH3:25])([CH3:24])[O:21][CH2:20][C:19]=2[CH2:26][OH:27])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][C:22]([CH3:24])([CH3:25])[O:21][CH2:20][C:19]=2[CH:26]=[O:27])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67126442HCID 67126442, compound

Product 1

HCID 87279390HCID 87279390, 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 38D (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. After filtration and evaporation of solvent, the crude product was loaded on a column and eluted with 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. filtrationAfter filtration and evaporation of solvent
  6. washeluted with 5% ethyl acetate in hexane
  7. customto give the product

Sources & evidence

ORD record
ord-cfd96a73ff7b46eb90cd7d34d08716c0
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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