Hydrogen Peroxide → HCID 70974766, compound

HRID 922704Notes

Reaction equation

HRID 922704 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([CH3:18])[CH2:9][NH:10][C:11]2[S:15][N:14]=[C:13]([C:16]#[N:17])[N:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:21].[K+].[K+].OO>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([CH3:18])[CH2:9][NH:10][C:11]2[S:15][N:14]=[C:13]([C:16]([NH2:17])=[O:21])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 70974879HCID 70974879, compound

Product 1

HCID 70974766HCID 70974766, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 0° C. mixture of 5-(2-(4-fluorophenyl)-2-methylpropylamino)-1,2,4-thiadiazole-3-carbonitrile (100 mg, 3.65 mmol, 1.0 equiv) and K2CO3 (202 mg, 14.6 mmol, 4.0 equiv) in DMSO (1.0 mL) was added hydrogen peroxide (30% in water, 1.1 mL, 36 mmol, 10 equiv) by syringe. After stirring for 15 min, the ice bath was removed, and the reaction mixture was stirred overnight. The reaction mixture was diluted with EtOAc and washed repeatedly with water and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Preparatory thin layer chromatography (5% MeOH/DCM) provided the title compound (17 mg, 16%). m/z=295 [M+H]+.

Workup

  1. customthe ice bath was removed
  2. stirringthe reaction mixture was stirred overnight
  3. additionThe reaction mixture was diluted with EtOAc
  4. washwashed repeatedly with water and once with brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-685909c4049d4975b8b28b29b671c243
Source dataset
uspto-grants-2016_03
Patent number
US09278962B2

Reaction notes

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