Potassium thiocyanate → HCID 86665171, compound

HRID 1893711Notes

Reaction equation

HRID 1893711 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([CH3:19])=[N:7][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:9]=1)=[O:4].[S-:20][C:21]#[N:22].[K+]>CC(C)=O.CCOC(C)=O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:8]2[CH:9]=[C:5]([C:3](=[O:4])[CH2:2][S:20][C:21]#[N:22])[C:6]([CH3:19])=[N:7]2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 516872Potassium thiocyanateHCID 86665170HCID 86665170, compound

Product 1

HCID 86665171HCID 86665171, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to Scheme 2, Step 3: To a solution of 2-bromo-1-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)ethanone (9.28 mmol, 3.00 g) in acetone (19 mL) was added potassium thiocyanate (9.28 mmol, 0.90 g) and the reaction mixture was stirred overnight at room temperature. Then, the reaction mixture was diluted with EtOAc and the organic phase was washed with water. The organic phase was dried over MgSO4, was filtered and was concentrated. The crude residue was purified by flash chromatography over silica gel using cyclohexane/EtOAc (80:20 to 50:50) as eluent to yield 1-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)-2-thiocyanatoethanone (6.57 mmol, 1.98 g, 71%).

Workup

  1. washthe organic phase was washed with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated
  5. customThe crude residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-313ce260a81a4b129bcc742523ecbeb5
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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