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

HRID 1164524Notes

Reaction equation

HRID 1164524 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-ec1e2ebe4b3344949e35c12f4dfcceb4
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

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