Dabco → 1-(3,4-Dichlorobenzyl)-3-cyano-6-methylpyrid-2-one

HRID 2418978Notes

Reaction equation

HRID 2418978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][NH:6][C:7](=[O:11])[CH2:8][C:9]#[N:10].CO[CH:18]=[CH:19][C:20](=O)[CH3:21].N12CCN(CC1)CC2>COCCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:5][N:6]1[C:20]([CH3:21])=[CH:19][CH:18]=[C:8]([C:9]#[N:10])[C:7]1=[O:11]

Participants

5

Reactant 3

HCID 9237DabcoHCID 942973-Buten-2-one, 4-methoxy-HCID 4168883N-(3,4-dichlorobenzyl)-2-cyanoacetamide

Product 1

HCID 203163511-(3,4-Dichlorobenzyl)-3-cyano-6-methylpyrid-2-oneYield 62%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 49.7 g. (0.204 mole) of N-(3,4-dichlorobenzyl)-2-cyanoacetamide, 48.0 g (0.48 mole) of 4-methoxy-3-buten-2-one, and 4 g. of 1,4-diazabicyclo (2.2.2)octane (DABCO) in 160 ml. of 2-methoxyethanol is refluxed for 4 hr. The dark reaction mixture is then concentrated in vacuo and the crude solid is isolated by filtration from the resulting slurry and washed with ether. The crude product is dissolved in methylene chloride and the organic solution is washed with water, 2N--HCl and finally with more water. The methylene chloride is removed and the product is obtained in 62% yield by ether tirituration.

Workup

  1. customThe dark reaction mixture
  2. concentrationis then concentrated in vacuo
  3. customthe crude solid is isolated by filtration from the resulting slurry
  4. washwashed with ether
  5. dissolutionThe crude product is dissolved in methylene chloride
  6. washthe organic solution is washed with water, 2N
  7. customThe methylene chloride is removed
  8. customthe product is obtained in 62% yield by ether tirituration

Sources & evidence

ORD record
ord-25c3b11dd47b4fa3b506626fb2417488
Source dataset
uspto-grants-1978_08
Patent number
US04104273

Reaction notes

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