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Acetamidomalonic acid diethyl ester → Diethyl 2-acetamido-2-(9-octadecenyl)malonate

HRID 862807
Notes
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Reaction equation

HRID 862807 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[O-]CC.[Na+].[CH2:20](Cl)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(O)C>[C:1]([NH:4][C:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 5580461-Chlorooctadec-9-eneHCID 2723922Sodium ethoxide

Product 1

HCID 53823167Diethyl 2-acetamido-2-(9-octadecenyl)malonateYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl 2-acetamidomalonate (15 g) was dissolved in 200 ml of dry ethanol and 5.6 g of sodium ethoxide was added thereto. To the reaction mixture, 22 g of 9-octadecenyl chloride was added while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with ethanol-concentrated hydrochloric acid (11:1) and concentrated. The concentrate was purified by silica gel column chromatography to give 1.3 g of diethyl 2-acetamido-2-(9-octadecenyl)malonate as a colorless, oily and viscous substance.

Workup

  1. temperaturethe mixture was refluxed for about 15 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22990285d8744f239be867f9e86305a0
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05719176

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes