Chlorzoxazone → HCID 117660476, compound

HRID 1428382Notes

Reaction equation

HRID 1428382 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 2733ChlorzoxazoneHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 117660476HCID 117660476, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under an argon atmosphere, to a mixture of 5-chloro-1,3-benzoxazol-2(3H)-one (50.0 g) and acetone (750 mL) were added K2CO3 (61.1 g) and tert-butyl bromoacetate (52.3 mL) at room temperature, followed by heating to reflux for 1.5 hours. The reaction mixture was filtered while hot, and washed with acetone. The filtrate and the washed solution were combined and concentrated under reduced pressure. The obtained solid was stirred with a mixed solvent of Hex/EtOAc (6/1) and collected by filtration, and further stirred with water and collected by filtration to obtain tert-butyl (5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate (81.1 g).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1.5 hours
  3. filtrationThe reaction mixture was filtered while hot, and
  4. washwashed with acetone
  5. concentrationconcentrated under reduced pressure
  6. filtrationcollected by filtration
  7. stirringfurther stirred with water
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5fe9253e935f406bb33f7ab471062699
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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