Pyridine → 2-[(3-Oxobutanoyl)amino]ethyl 2-methylprop-2-enoate

HRID 905104

Reaction equation

HRID 905104 reaction equation
N1C=CC=CC=1.Cl.[C:8]([O:13][CH2:14][CH2:15][NH2:16])(=[O:12])[C:9]([CH3:11])=[CH2:10].[CH2:17]=[C:18]1[O:22][C:20](=[O:21])[CH2:19]1>CN(C)C=O>[C:8]([O:13][CH2:14][CH2:15][NH:16][C:20](=[O:21])[CH2:19][C:18]([CH3:17])=[O:22])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12661DiketeneHCID 75495Aminoethyl methacrylate hydrochloride

Product 1

HCID 220239722-[(3-Oxobutanoyl)amino]ethyl 2-methylprop-2-enoateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Pyridine (16 g, 0.2 mole) was added dropwise at 0° C. to a solution of 2-aminoethyl methacrylate hydrochloride (33 g, 0.2 mole) and diketene (16.8 g, 0.2 mole) in N,N-dimethylformamide (600 ml). After the addition, the solution was stirred at 20° C. for 20 hours. The solvent was then removed at low vacuum. The residue was dissolved in chloroform (1200 ml), washed with water (twice with 200 ml), dried over anhydrous magnesium sulfate and filtered. Excess solvent was then removed. Distillation of the residue gave acetoacetamidoethyl methacrylate (b.p.=113°-132° C./5μ) at a yield of 60%.

Workup

  1. additionAfter the addition
  2. customThe solvent was then removed at low vacuum
  3. dissolutionThe residue was dissolved in chloroform (1200 ml)
  4. washwashed with water (twice with 200 ml),
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customExcess solvent was then removed
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-4af832bd7cb74f51a2e5b5031ea5f5d0
Source dataset
uspto-grants-1983_12
Patent number
US04421915

Linked notes

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