Dimethyl Sulfoxide → HCID 59730256, compound

HRID 130959Notes

Reaction equation

HRID 130959 reaction equation
OO.[F:3][C:4]1[C:18]([F:19])=[C:17]([CH:20]=[O:21])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][N:8]=1.C([O-])([O-])=[O:23].[K+].[K+].CS(C)=O>O>[F:3][C:4]1[C:18]([F:19])=[C:17]([CH:20]=[O:21])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]([NH2:12])=[O:23])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 59730380HCID 59730380, compound

Product 1

HCID 59730256HCID 59730256, compoundYield 148.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 30% aq. H2O2 (7.95 ml) to a suspension of 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinonitrile (2.07 g, 7.95 mmol), K2CO3 (550 mg, 3.98 mmol) and DMSO (20 ml) stirring in an ice/water bath. After one hour, pour the reaction mixture into water and extract with EtOAc. Wash the extract with water and brine before drying (MgSO4) and concentrating to give 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinamide (1.64 g) as a white solid. 1HNMR (DMSO-d6): 10.14 (s, 1H), 8.58 (s, 1H), 8.33 (d, 1H), 8.07 (s, 1H), 7.74 (t, 1H), 7.55 (s, 1H), 7.33 (d, 1H), 7.27 (t, 1H).

Workup

  1. extractionextract with EtOAc
  2. washWash the
  3. extractionextract with water and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-f455e105f3cd433990dea61c1867cd20
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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