N-bromobutanimide → HCID 67384081, compound

HRID 1471900Notes

Reaction equation

HRID 1471900 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH2:12][CH2:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([CH2:12][CH2:13][CH3:14])[NH:10][N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67384919HCID 67384919, compound

Product 1

HCID 67384081HCID 67384081, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

To a solution of 4-phenyl-5-propyl-1H-pyrazole (1.43 g, 7.68 mmol) in acetonitrile (38.0 mL), was added N-bromosuccinimide (1.50 g, 8.45 mmol). The reaction mixture was stirred at 82° C. After 16 h, the reaction mixture was quenched with 2 M Na2CO3 (aq.) to pH 12 and the organics were separated. The aqueous layer was extracted with EtOAc (3×). The combined organics were dried over MgSO4, filtered and concentrated to give a dark oil. This oil was purified by silica gel flash chromatography to give the title compound as a yellow oil (0.310 g). LCMS m/z=265.1, 267.1 [M+H]+.

Workup

  1. customthe reaction mixture was quenched with 2 M Na2CO3 (aq.) to pH 12
  2. customthe organics were separated
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a dark oil
  8. customThis oil was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-948d8f67111f45a7967fb5faef1cbe4a
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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