Potassium Carbonate → HCID 20555481, compound

HRID 1105494Notes

Reaction equation

HRID 1105494 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([S:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:8]=[N:9][C:4]=2[CH:3]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([S:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][CH:16]=3)[N:8]=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 20555482HCID 20555482, compound

Product 1

HCID 20555481HCID 20555481, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-[(7-chloro-1,2,4-benzotriazin-3-yl)thio]phenol (1.83 g), ethyl 2-bromopropionate (1.37 g), anhydrous potassium carbonate (0.96 g) and methyl ethyl ketone (50 ml) was heated under reflux for a period of 3 hours. The solvent was removed by distillation under reduced pressure and the residue was partitioned between water and dichloromethane. The organic phase was separated, dried (over anhydrous magnesium sulfate) and the solvent was removed by distillation under reduced pressure to give a solid. The crude product was purified by chromatography over silica gel (eluent dichloromethane) to give the title compound (1.95 g) as a crystalline solid, mp 86°-88° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 3 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was partitioned between water and dichloromethane
  5. customThe organic phase was separated
  6. dry with materialdried (over anhydrous magnesium sulfate)
  7. customthe solvent was removed by distillation under reduced pressure
  8. customto give a solid
  9. customThe crude product was purified by chromatography over silica gel (eluent dichloromethane)

Sources & evidence

ORD record
ord-953495788e62452e96f244dcfcb8e6d5
Source dataset
uspto-grants-1982_01
Patent number
US04309211

Reaction notes

Loading…