N-bromobutanimide → HCID 86646794, compound

HRID 2425540Notes

Reaction equation

HRID 2425540 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](=[O:10])C)[CH:4]=[N:3]1.[Br:11]N1C(=O)CCC1=O>C1COCC1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[CH:4][C:5]=1[CH:8]=[O:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 70194271-(1,5-dimethyl-1H-pyrazol-4-yl)ethanone

Product 1

HCID 86646794HCID 86646794, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(1,5-dimethyl-1H-pyrazol-4-yl)ethanone (471 mg, 3.42 mmol) in THF (13 ml) was added N-bromosuccinimide (637 mg, 3.58 mmol) and benzoyl peroxide (41 mg, 0.17 mmol) at room temperature under nitrogen, then the resulting mixture was refluxed for 20 h. After cooling, the reaction mixture was evaporated to remove the solvents. The residue was chromatographed on a column of silica gel eluting with ethyl acetate-hexane (1:1) gave the title compound as white solid (574 mg, 78% yield). 1H NMR (270 MHz, CDCl3) 2.47 (3H, s), 3.91 (3H, s), 4.87 (2H, s), 7.83 (1H, s). MS (ESI) m/z: 217 (M+H)+.

Workup

  1. temperaturethe resulting mixture was refluxed for 20 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. customto remove the solvents
  5. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-979b3ff1591c4a0f9986c7a856d38313
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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