Allyl bromide → HCID 21545962, compound

HRID 1606101Notes

Reaction equation

HRID 1606101 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]2=[O:17].[CH2:18](Br)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]2=[O:17])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 23336681HCID 23336681, compound

Product 1

HCID 21545962HCID 21545962, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 12.5 parts of ethyl 6-hydroxy-1-thiachromone-2-carboxylate, 6.8 parts of allyl bromide and 9.7 parts of anhydrous potassium carbonate in 80 parts of acetone was heated under reflux for 20 hours. The mixture was filtered and the solution was evaporated. The residual material was dissolved in chloroform and the solution was washed with water, then the chloroform was evaporated and the remaining material was crystallised from ethanol to give 11.8 parts of ethyl 6-allyloxy-1-thiachromone-2-carboxylate, melting point, 107.5°-8°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe mixture was filtered
  4. customthe solution was evaporated
  5. dissolutionThe residual material was dissolved in chloroform
  6. washthe solution was washed with water
  7. customthe chloroform was evaporated
  8. customthe remaining material was crystallised from ethanol

Sources & evidence

ORD record
ord-4ada675d7ea64287bcbb01ca038a6908
Source dataset
uspto-grants-1976_04
Patent number
US03952013

Reaction notes

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