3-Pyridinecarboxaldehyde → HCID 70252295, compound

HRID 1636310Notes

Reaction equation

HRID 1636310 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[ClH:9].[NH2:10][N:11]1[CH2:15][CH:14]([CH3:16])[N:13]([CH3:17])[C:12]1=[O:18]>CO>[ClH:9].[CH3:17][N:13]1[CH:14]([CH3:16])[CH2:15][N:11]([N:10]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:12]1=[O:18]

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 19350747HCID 19350747, compound

Product 1

HCID 70252295HCID 70252295, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.3 g of pyridine-3-carbaldehyde are added at room temperature to a solution of 3.6 g of 1-amino-3,4-dimethylimidazolidin-2-one hydrochloride in 25 ml of methanol. The solution is concentrated by evaporation and the residue is stirred with tetrahydrofuran. 4.6 g of 3,4-dimethyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one hydrochloride having a melting point of 232-236° are obtained. 2.3 g of triethylamine are added to a suspension of 4.4 g of 3,4-dimethyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one hydrochloride in 100 ml of tetrahydrofuran and after 20 minutes under reflux the reaction mixture is filtered while hot. 300 ml of hexane are added to the filtrate. The crystals that have precipitated are filtered off with suction and dried. 2.5 g of the title compound having a melting point of 126-129° are obtained.

Workup

  1. concentrationThe solution is concentrated by evaporation

Sources & evidence

ORD record
ord-7bb209f54ed7494b8ce2d5e7c7f329a2
Source dataset
uspto-grants-2000_03
Patent number
US06034083

Reaction notes

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