Dimethyl Sulfoxide → HCID 59750675, compound

HRID 422207Notes

Reaction equation

HRID 422207 reaction equation
OO.[CH3:3][C:4]1[C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:22].C([O-])([O-])=[O:24].[K+].[K+].CS(C)=O>O>[CH3:3][C:4]1[C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]([NH2:19])=[O:24])=[CH:16][N:15]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:22]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66673442HCID 66673442, compound

Product 1

HCID 59750675HCID 59750675, compoundYield 164.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 30% aqueous H2O2 (3.6 ml) to a suspension of 6-(4-Methyl-1-oxo-indan-5-yloxy)-nicotinonitrile (1.22 mg, 4.61 mmol), K2CO3 (319 mg, 2.31 mmol) and DMSO (20 ml) stirring under nitrogen at ambient temperature. After 2.5 hours, dilute the reaction mixture with water (100 ml) and extract with EtOAc (2×). Wash the extract with water and brine, dry (MgSO4) and concentrate on rotary evaporator to yield 1.07 g of the title compound as a yellow solid. Mass spectrum (ion spray): m/z=283 (M+1); 1HNMR (DMSO-d6): 8.55 (s, 1H), 8.27 (d, 1H), 8.01 (s, 1H), 7.51 (d, 1H), 7.47 (s, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 3.03 (t, 2H), 2.66 (t, 2H), 2.07 (s, 3H).

Workup

  1. extractionextract with EtOAc (2×)
  2. washWash the
  3. extractionextract with water and brine
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate on rotary evaporator

Sources & evidence

ORD record
ord-f7a5b5522a1940a8a134833a14cb536a
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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