Sodium Bicarbonate → HCID 23333616, compound

HRID 904182Notes

Reaction equation

HRID 904182 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].Br[CH2:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O>[CH3:1][N:2]([CH2:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11032082Ethyl 2-(bromomethyl)benzoateHCID 11550151N-methyl-4-ethoxycarbonylmethylaniline

Product 1

HCID 23333616HCID 23333616, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-methyl-4-ethoxycarbonylmethylaniline (10 g), sodium hydrogencarbonate (5 g) and water (5 ml) was heated to 90° C. on an oil bath. Ethyl 2-bromomethylbenzoate (12.2 g) was gradually added dropwise to the mixture with stirring. Then, the mixture was stirred for 2 hours at 90° C. The reaction mixture was cooled, and extracted with benzene. The extract was washed with water. The benzene layer was extracted with 2 N-HCl. The aqueous layer was neutralized with potassium carbonate while cooling the layer with ice, and extracted with benzene. The benzene layer was dried over anhydrous magnesium sulfate. When the solvent was distilled off under reduced pressure, 20 g of N-methyl-N(2-ethoxycarbonylbenzyl)-4-ethoxycarbonylmethylaniline was obtained as a light-yellow oily material.

Workup

  1. stirringThen, the mixture was stirred for 2 hours at 90° C
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with benzene
  4. washThe extract was washed with water
  5. extractionThe benzene layer was extracted with 2 N-HCl
  6. temperaturewhile cooling the layer with ice
  7. extractionextracted with benzene
  8. dry with materialThe benzene layer was dried over anhydrous magnesium sulfate
  9. distillationWhen the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4d00114f1fd645269cc02d5db5861252
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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