Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 20329878, compound

HRID 2058084Notes

Reaction equation

HRID 2058084 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([N:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 4592750HCID 4592750, compoundHCID 5360545Sodium

Product 1

HCID 20329878HCID 20329878, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a) To 60 ml of absolute ethanol is added 0.58 g of sodium, and 4.6 g of 4-[N-(3-chlorophenyl)formimidoyl]phenol and then 5.84 g of ethyl 2-bromo-2-methylpropionate are added to the solution at room temperature with stirring. The mixture is refluxed under heating and with stirring for 5 hours. After distilling off the ethanol from the reaction mixture, the residue is dissolved in ether. The solution is washed with 5% aqueous solution of sodium hydroxide until disappearance of the color of the aqueous layer, then washed with water and dried. After drying, the solvent is distilled off to give 4.1 g of ethyl 2-[4-{N-(3-chlorophenyl)formimidoyl}phenoxy]-2-methylpropionate.

Workup

  1. temperatureThe mixture is refluxed
  2. temperatureunder heating
  3. stirringwith stirring for 5 hours
  4. distillationAfter distilling off the ethanol from the reaction mixture
  5. dissolutionthe residue is dissolved in ether
  6. washThe solution is washed with 5% aqueous solution of sodium hydroxide until disappearance of the color of the aqueous layer
  7. washwashed with water
  8. customdried
  9. customAfter drying
  10. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-212de5bc98814884b79eef1c4e5b9272
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

Loading…