N-bromobutanimide → HCID 21251141, compound

HRID 1532026Notes

Reaction equation

HRID 1532026 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][O:5][C:4]([C:7]2[O:11][N:10]=[C:9]([O:12][CH2:13][CH3:14])[C:8]=2[CH3:15])=[N:3]1.C1C(=O)N([Br:24])C(=O)C1>ClC(Cl)(Cl)Cl>[Br:24][CH2:15][C:8]1[C:9]([O:12][CH2:13][CH3:14])=[N:10][O:11][C:7]=1[C:4]1[O:5][CH2:6][C:2]([CH3:1])([CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21251137HCID 21251137, compound

Product 1

HCID 21251141HCID 21251141, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-(4,5-Dihydro-4,4-dimethyl-1,3-oxazol-2-yl)-3-ethoxy-4-methylisoxazole (2.0 g, 8.9 mmol), NBS (1.75 g, 9.8 mmol) and tetrachloromethane (150 mL) was boiled under reflux for 5 h. The mixture was cooled, filtered and concentrated in vacuo. Flash chromatography (silica gel, eluent: toluene/EtOAc/triethylamine=100:10:1) gave the title compound as a yellow oil (2.0 g, 74%).

Workup

  1. temperatureunder reflux for 5 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38ff6b102d194f7fbb8a532f74e3cbad
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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