Dimethyl Sulfoxide → 854758-37-5

HRID 1174318Notes

Reaction equation

HRID 1174318 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:15]1[N:20]=[C:19]([CH2:21][OH:22])[CH:18]=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([C:15]1[N:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20709528HCID 20709528, compound

Product 1

HCID 58790019854758-37-5Yield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of DMSO (0.90 mL, 12.7 mmol) in dichloromethane (10 mL) at −78° C. was treated with oxalyl chloride (3.1 mL, 2 M in dichloromethane) dropwise, stirred for an additional 15 minutes at −78° C., treated with a solution of the product from Example 115E (0.88 g, 5.3 mmol) in dichloromethane (14 mL) over 10 minutes, stirred for 20 minutes, treated dropwise with triethylamine (3.6 mL, 26.1 mmol) at −78° C., stirred for 10 minutes, warmed to 0° C., stirred for an additional 10 minutes, quenched with water and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform to give the title compound (0.77 g, 88% yield).

Workup

  1. stirringstirred for 20 minutes
  2. stirringstirred for 10 minutes
  3. temperaturewarmed to 0° C.
  4. stirringstirred for an additional 10 minutes
  5. customquenched with water
  6. custompartitioned between dichloromethane and water
  7. washThe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform

Sources & evidence

ORD record
ord-6a8ded885c69407a8e386ba01f1c7a6f
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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