Methyl iodide → HCID 575660, compound

HRID 1639170Notes

Reaction equation

HRID 1639170 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].[H-].[Na+].[CH3:18]I>O1CCCC1>[C:1]([NH:4][C:5]([CH3:18])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydride

Product 1

HCID 575660HCID 575660, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl 2-acetylaminomalonate (2.17 g) in dry tetrahydrofuran is added sodium hydride (0.26 g), and the mixture is stirred at room temperature for one hour. After stirring, methyl iodide (1.60 g) is added dropwise thereto, and the mixture is stirred overnight. The reaction mixture is concentrated, and to the residue is added ethyl acetate and water. The organic layer is separated, dried and evaporated to remove the solvent. The residue is recrystallized from a mixture of isopropyl ether and n-hexane to give diethyl 2-acetylamino-2-methylmalonate (1.80 g), m.p. 89°-90° C.

Workup

  1. stirringAfter stirring
  2. stirringthe mixture is stirred overnight
  3. concentrationThe reaction mixture is concentrated
  4. additionto the residue is added ethyl acetate and water
  5. customThe organic layer is separated
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is recrystallized from a mixture of isopropyl ether and n-hexane

Sources & evidence

ORD record
ord-800b844e79b84cd7bbd53889fbbf3150
Source dataset
uspto-grants-1989_11
Patent number
US04882447

Reaction notes

Loading…