N-bromobutanimide → 5-(Adamantan-1-yloxymethyl)-4-bromo-2-cyclohexyl-1,2-dihydro-pyrazol-3-one

HRID 967803Notes

Reaction equation

HRID 967803 reaction equation
[C:1]12([O:11][CH2:12][C:13]3[CH:14]=[C:15]([OH:24])[N:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)[N:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Br:25]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[C:1]12([O:11][CH2:12][C:13]3[NH:17][N:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)[C:15](=[O:24])[C:14]=3[Br:25])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178516267HCID 178516267, compound

Product 1

HCID 222919835-(Adamantan-1-yloxymethyl)-4-bromo-2-cyclohexyl-1,2-dihydro-pyrazol-3-oneYield 48.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A CCl4 solution (10 mL) of 5-(adamantan-1-yloxymethyl)-2-cyclohexyl-2H-pyrazol-3-ol (0.11 g, 0.33 mmol), azobisisobutyronitrile (2 mg) and N-bromosuccinimide (70 mg, 0.4 mmol) was irradiated by a 100 W light source for 0.3 h at rt. After filtration to the filtrate was concentrated in vacuo to afford a crude product as a purple solid, which was purified by chromatography with EtOAc-DCM (1:4) as eluant. The product was obtained as a white glassy solid (65 mg, 48%).

Workup

  1. filtrationAfter filtration to the filtrate
  2. concentrationwas concentrated in vacuo
  3. customto afford a crude product as a purple solid, which
  4. customwas purified by chromatography with EtOAc-DCM (1:4) as eluant

Sources & evidence

ORD record
ord-dff94910c1764cc589a4e08b1d3ec9e8
Source dataset
uspto-grants-2005_10
Patent number
US06956053B2

Reaction notes

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