Chlorzoxazone → HCID 19900718, compound

HRID 1029474Notes

Reaction equation

HRID 1029474 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]2[NH:8][C:9]([O:11][C:3]=2[CH:2]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]#[CH:20]>CC(C)=O>[CH2:20]([N:8]1[C:4]2[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=2[O:11][C:9]1=[O:10])[C:19]#[CH:18]

Participants

5

Reactant 3

HCID 2733Chlorzoxazone2×HCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 19900718HCID 19900718, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 500-mL round bottom flask equipped with a magnetic stirrer, reflux condenser and a heating mantle were placed chlorzoxazone, or 5-chlorobenzoxazol-2-one, (10 g, 0.059 mole), potassium carbonate (9.8 g, 0.071 mole), propargyl bromide (10.5 g of 80% in toluene, 0.071 mole) and acetone (200 mL). The mixture was refluxed for 20 hours. The mixture was cooled down to room temperature and the solid was filtered off by suction-filtration. The filtrate was concentrated on a rotary evaporator to a solid residue. A pure, off-white product was obtained by crystallization from ethyl acetate hexane yielding 10.5 g (86%). m.p.

Workup

  1. customIn a 500-mL round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was refluxed for 20 hours
  4. filtrationthe solid was filtered off by suction-filtration
  5. concentrationThe filtrate was concentrated on a rotary evaporator to a solid residue
  6. customA pure, off-white product was obtained by crystallization from ethyl acetate hexane yielding 10.5 g (86%)

Sources & evidence

ORD record
ord-214f01fd460544cfbd123311eb8ff94c
Source dataset
uspto-grants-1992_04
Patent number
US05102898

Reaction notes

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