Dimethyl Sulfoxide → HCID 58542326, compound

HRID 1951899Notes

Reaction equation

HRID 1951899 reaction equation
C(OC(=O)C)(=O)C.CS(C)=O.[C:12]([O:16][C:17](=[O:38])[NH:18][C:19]([C:31]1[CH:32]=[N:33][C:34]([Cl:37])=[CH:35][CH:36]=1)([CH3:30])[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([F:29])[CH:23]=1)[OH:21])([CH3:15])([CH3:14])[CH3:13]>C(OCC)(=O)C>[C:12]([O:16][C:17](=[O:38])[NH:18][C:19]([C:31]1[CH:32]=[N:33][C:34]([Cl:37])=[CH:35][CH:36]=1)([CH3:30])[C:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([F:29])[CH:23]=1)=[O:21])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 58542355HCID 58542355, compound

Product 1

HCID 58542326HCID 58542326, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (2.3 ml, 24.7 mmol) was added to a dimethyl sulfoxide (8 ml) solution of the compound (1.14 g, 2.75 mmol) obtained in Step 4 above under ice cooling and the resulting mixture was gradually returned to room temperature while being stirred for 18 hours. The reaction mixture was diluted with ethyl acetate, washed with 6% aqueous sodium perchlorate solution, 10% aqueous sodium thiosulfate solution, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)] to give the title compound (1.10 g, 97%) as a pale yellow solid.

Workup

  1. customwas gradually returned to room temperature
  2. washwashed with 6% aqueous sodium perchlorate solution, 10% aqueous sodium thiosulfate solution, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)]

Sources & evidence

ORD record
ord-004601a9efc144a4b1f6a8ce288e28eb
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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