Sodium Iodide → HCID 53712490, compound

HRID 2188221Notes

Reaction equation

HRID 2188221 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8]([NH:14][C:15]([CH3:17])=[O:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].[I-].[Na+].[C:20]([NH:23][CH2:24][C:25]#[C:26][CH2:27]Cl)(=[O:22])[CH3:21]>O1CCOCC1.C(O)C>[CH2:12]([O:11][C:9](=[O:10])[C:8]([NH:14][C:15](=[O:16])[CH3:17])([CH2:27][C:26]#[C:25][CH2:24][NH:23][C:20](=[O:22])[CH3:21])[C:6]([O:5][CH2:4][CH3:3])=[O:7])[CH3:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 15177015N-(4-Chlorobut-2-yn-1-yl)acetamide

Product 1

HCID 53712490HCID 53712490, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent3×

Procedure

To a cold (0° C.) solution of sodium hydride (60% dispersion in mineral oil, 3.48 g) in dioxane (70 ml) was added dropwise absolute ethanol (70 ml). The mixture was allowed to warm to room temperature and a solution of diethyl acetamido malonate (20.5 g) in dioxane (70 ml) was added dropwise. Sodium iodide (9.07 g) was added and a solution of 1-acetylamino-4-chloro-2-butyne (11 g) in dioxane (140 ml) was added dropwise at room temperature. After addition of another 100 ml of ethanol the mixture was refluxed for 2.5 h. The reaction mixture was cooled and the precipitate formed was filtered off. Purification using chromatography on silica (eluent: ethyl acetate/methanol 9/1 v/v) yielded acetamido(4-acetamido-2-butynyl)-malonic acid diethyl ester. (15.9 g).

Workup

  1. temperaturewas refluxed for 2.5 h
  2. temperatureThe reaction mixture was cooled
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. customPurification

Sources & evidence

ORD record
ord-a12df2f424f345e9ac6dc9a4f712b99d
Source dataset
uspto-grants-2002_06
Patent number
US06410684B1

Reaction notes

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