Acetamidomalonic acid diethyl ester → Diethyl 2-acetylamino-2-(3,4-dimethylbenzyl)malonate

HRID 584220Notes

Reaction equation

HRID 584220 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5]Cl.[C:11]([NH:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12].[O-]CC.[Na+]>C(O)C>[C:11]([NH:14][C:15]([CH2:5][C:4]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:2]([CH3:1])[CH:3]=1)([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 660183,4-Dimethylbenzyl chlorideHCID 2723922Sodium ethoxide

Product 1

HCID 13406779Diethyl 2-acetylamino-2-(3,4-dimethylbenzyl)malonateYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dimethylbenzyl chloride (10.2 g) and diethyl acetamidomalonate (14.3 g) were added successively into a solution of sodium ethoxide (4.94 g) in ethanol. The mixture was stirred under reflux for 2 hours and filtered through Celite®. The filtrate was concentrated under reduced pressure to give crystals which were collected by filtration and washed with isopropyl ether to give colorless crystals of diethyl 2-acetylamino-2-(3,4-dimethylbenzyl)malonate (11.8 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give crystals which
  5. filtrationwere collected by filtration
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-3c805eeadff34d75a8c4d32cef27e858
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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