Ethyl bromoacetate → Ethyl 2-oxo-4-phenoxy-3-benzothiazolineacetate

HRID 1903737Notes

Reaction equation

HRID 1903737 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:1]=[C:2]1[N:6]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2[C:7]([O:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 130970844-Phenoxy-1,3-benzothiazol-2(3H)-one

Product 1

HCID 13097085Ethyl 2-oxo-4-phenoxy-3-benzothiazolineacetateYield 73.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-oxo-4-phenoxybenzothiazoline (2.0 g), ethyl bromoacetate (1.7 g), potassium carbonate (1.4 g) in acetone (30 ml) was refluxed for an hour with stirring. After the resultant mixture was filtered, the filtrate was concentrated under reduced pressure to give a residue, which was recrystallized from a mixture of ethanol and n-hexane to give crystalline ethyl 2-oxo-4-phenoxy-3-benzothiazolineacetate (2.0 g).

Workup

  1. temperaturewas refluxed for an hour
  2. filtrationAfter the resultant mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a residue, which
  5. customwas recrystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-1729a752dcda40d39eb7612fde19f682
Source dataset
uspto-grants-1984_03
Patent number
US04438126

Reaction notes

Loading…