Potassium Carbonate → HCID 178424079, compound

HRID 1471902Notes

Reaction equation

HRID 1471902 reaction equation
[C:1]1([CH:7]2[C:11](=[S:12])[NH:10][N:9]=[C:8]2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C:26]2[C:27](C3C=CC(C)=CC=3)=[N:28]NC=2SSC2NN=C(C3C=CC(C)=CC=3)C=2C2C=CC=CC=2)C=CC=CC=1.BrCC#N.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]1([C:7]2[C:8]([C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)=[N:9][NH:10][C:11]=2[S:12][CH2:26][C:27]#[N:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86657581HCID 86657581, compoundHCID 178424081HCID 178424081, compound

Product 1

HCID 178424079HCID 178424079, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 4-phenyl-3-p-tolyl-1H-pyrazole-5(4H)-thione and 1,2-bis(4-phenyl-3-p-tolyl-1H-pyrazol-5-yl)disulfane (0.500 g, 1.88 mmol) in DMF (12.5 mL) was added 2-bromoacetonitrile (0.125 mL, 1.88 mmol) and K2CO3 (0.259 g, 1.88 mmol). The reaction was stirred at 25° C. for 72 h, quenched with water (40.0 mL) and extracted with EtOAc (4×50.0 mL) and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated to give the title compound as a yellow oil (0.547 g). LCMS m/z=306.2 [M+H]+.

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

Sources & evidence

ORD record
ord-27956ae69eea438f9da6dbf89587313a
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

Loading…