Ethyl bromoacetate → 2-(trans-3-Ethoxycarbonylmethoxystyryl)benzothiazole

HRID 1199705Notes

Reaction equation

HRID 1199705 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:24]([O:23][C:21]([CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 7986269HCID 7986269, compound

Product 1

HCID 140511752-(trans-3-Ethoxycarbonylmethoxystyryl)benzothiazoleYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 30 ml of acetone were added 200 mg of 2-(trans-3-hydroxystyryl)benzothiazole, 0.11 ml of ethyl bromoacetate and 131 mg of potassium carbonate, and the mixture was refluxed for 4 hours. After cooled to room temperature, the mixture was extracted with ethyl ether, dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. After the crude crystals of the residue were washed with ethyl ether and n-hexane, they were dried under reduced pressure to give 207 ml (yield 77%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. extractionthe mixture was extracted with ethyl ether
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washAfter the crude crystals of the residue were washed with ethyl ether and n-hexane, they
  6. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-33abe700bcb745738dd16b41f5f9c8a4
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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