Potassium Carbonate → HCID 178489652, compound

HRID 1471903Notes

Reaction equation

HRID 1471903 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:13](=[S:14])[NH:12][N:11]=[C:10]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7][CH:8]=1.Br[CH2:22][C:23]#[N:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][NH:12][C:13]=2[S:14][CH2:22][C:23]#[N:24])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86657583HCID 86657583, compound

Product 1

HCID 178489652HCID 178489652, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(3-methoxyphenyl)-3-phenyl-1H-pyrazole-5(4H)-thione (0.200 g, 0.708 mmol) in DMF (5.0 mL) was added 2-bromoacetonitrile (0.047 mL, 0.708 mmol) and K2CO3 (0.098 g, 0.708 mmol). The mixture was stirred at 25° C. for 72 h, quenched with water (40.0 mL), extracted with EtOAc (4×50.0 mL) and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated to give a brown oil. This brown oil was purified by silica gel flash chromatography to give the title compound as a white solid (0.158 g). LCMS m/z=332.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 3.67 (s, 2H), 3.74 (s, 3H), 6.82-6.89 (m, 3H), 7.23-7.29 (m, 1H), 7.34 (s, 5H).

Workup

  1. customquenched with water (40.0 mL)
  2. extractionextracted with EtOAc (4×50.0 mL)
  3. washwashed with brine
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThis brown oil was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-b48f0493e8e94624a8e908d5dda8e794
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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