Potassium Carbonate → HCID 20555479, compound

HRID 1105493Notes

Reaction equation

HRID 1105493 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7](Cl)[N:8]=[N:9][C:4]=2[CH:3]=1.[OH:13][C:14]1[CH:27]=[CH:26][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7]([O:13][C:14]3[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:26][CH:27]=3)[N:8]=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterHCID 20555480HCID 20555480, compound

Product 1

HCID 20555479HCID 20555479, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 7-bromo-3-chloro-1,2,4-benzotriazine (1.93 g), ethyl 2-(4-hydroxyphenoxy)propionate (1.69 g), anhydrous potassium carbonate (1.20 g) and methyl ethyl ketone (50 ml) was heated under reflux overnight. The solvent was removed by distillation under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was separated, dried (over anhydrous magnesium sulfate) and the solvent was removed by distillation under reduced pressure to give an oil. The crude product was purified by chromatography over silica gel (eluent dichloromethane) and the product was recrystallised from aqueous ethanol to give the title compound (1.16 g) as yellow crystals, mp 104° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was partitioned between water and dichloromethane
  5. customThe organic layer was separated
  6. dry with materialdried (over anhydrous magnesium sulfate)
  7. customthe solvent was removed by distillation under reduced pressure
  8. customto give an oil
  9. customThe crude product was purified by chromatography over silica gel (eluent dichloromethane)
  10. customthe product was recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-a748d357aabf4a839eeab5c8d2756a29
Source dataset
uspto-grants-1982_01
Patent number
US04309211

Reaction notes

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