Acetamidomalonic acid diethyl ester → HCID 232194, compound

HRID 2259295Notes

Reaction equation

HRID 2259295 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21]Br>C(O)C>[CH2:10]([O:9][C:7](=[O:8])[C:6]([NH:5][C:2](=[O:4])[CH3:3])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:21][C:20]1[CH:23]=[CH:24][C:25]([Cl:26])=[C:18]([Cl:17])[CH:19]=1)[CH3:11]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 5360545Sodium

Product 1

HCID 232194HCID 232194, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium pellets were dissolved in ethanol (200 ml). Diethyl acetamidomalonate (6.53 g) was added and the solution stirred for 30 minutes. 3,4-Dichlorobenzyl bromide (10.0 g), was added and the solution refluxed for 3.5 hours. The solution was filtered whilst hot and allowed to cool before water (200 ml) was added. On standing at 4° C. for 12 hours the title compound precipitated as colourless crystals which were removed by filtration and dried under vacuum (9.27 g). 1H NMR (360 MHz, CDCl3) δ7.32 (1H, d, J=8 Hz), 7.10 (1H, d, J=2 Hz), 6.85 (1H, dd, J=8, 2 Hz), 6.55 (1H, s), 4.28 (2H, m), 3.62 (2H, s), 2.05 (3H, s), 1.3 (3H, t, J=7 Hz).

Workup

  1. temperaturethe solution refluxed for 3.5 hours
  2. filtrationThe solution was filtered whilst hot and
  3. temperatureto cool before water (200 ml)
  4. additionwas added
  5. waitOn standing at 4° C. for 12 hours
  6. customthe title compound precipitated as colourless crystals which
  7. customwere removed by filtration
  8. customdried under vacuum (9.27 g)

Sources & evidence

ORD record
ord-02cde570cfac4e66942c7e385fd4c53d
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

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