Dimethyl Sulfoxide → HCID 58847106, compound

HRID 1820639Notes

Reaction equation

HRID 1820639 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[CH:17]=[O:18])[CH2:3]1.C(=O)([O-])[O-:20].[K+].[K+].OO.CS(C)=O>CC(C)=O.[Cl-].[Na+].O>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([C:13]([NH2:14])=[O:20])=[CH:11][C:10]=2[CH:17]=[O:18])[CH2:3]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen Peroxide2×HCID 11430Potassium Carbonate2×HCID 58847064HCID 58847064, compound

Product 1

HCID 58847106HCID 58847106, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-(cis-2,6-dimethylmorpholin-4-yl)-3-formylbenzonitrile (Example 6, Step 1) (0.244 g, 1.00 mmol) in acetone (4 mL) is treated with anhydrous powdered potassium carbonate (0.028 g, 0.20 mmol) followed by 30% hydrogen peroxide (0.204 g, 6.00 mmol).The reaction mixture is stirred at room temperature. After 24 h, additional 30% hydrogen peroxide (6.0 mmol) and acetone (2 mL) is added. After stirring at RT for 5 days, an additional potassium carbonate (0.96 g) and DMSO (4 mL) is added and stirred at RT for 24 h. The reaction mixture is poured into 50% saturated brine (40 mL), extracted with ether (3×), dried (NaSO4) and concentrated. The resulting residue is purified by silica gel chromatography using acetone-methylene chloride (1:4) as the eluent, to afford 28 mg (11%) of the desired amide as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 10.20, 8.20, 8.09, 7.12, 6.47-5.88, 4.00-3.86, 3.20, 2.74, 1.25.

Workup

  1. stirringAfter stirring at RT for 5 days
  2. stirringstirred at RT for 24 h
  3. extractionextracted with ether (3×)
  4. dry with materialdried (NaSO4)
  5. concentrationconcentrated
  6. customThe resulting residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-0aff73aa1be44d8b90ba4fe3e8a964bb
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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