3-Pyridinecarboxaldehyde → HCID 70338555, compound

HRID 1489507Notes

Reaction equation

HRID 1489507 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)=O.[NH2:9][N:10]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[NH:12][C:11]1=[O:19]>Cl.C(O)C>[O:19]=[C:11]1[NH:12][C:13]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:14][N:10]1[N:9]=[CH:1][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 22901846HCID 22901846, compound

Product 1

HCID 70338555HCID 70338555, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

5.4 g of 3-formylpyridine and three drops of concentrated hydrochloric acid are added to a solution of 7.8 g of 1-amino-2,3-dihydro-2-oxo4-tert-butyl-1H-imidazole in 50 ml of ethanol. The reaction mixture is refluxed for 30 minutes with stirring and then cooled to room temperature, upon which the mixture starts to crystallize. To complete the crystal precipitation process, 100 ml of diethyl ether are added to the mixture. The crystallizate is filtered off with suction, triturated with acetonitrile, again filtered off with suction and then dried. This gives the title compound which melts at 255°-256°.

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes
  2. customto crystallize
  3. customTo complete the crystal precipitation process, 100 ml of diethyl ether
  4. additionare added to the mixture
  5. filtrationThe crystallizate is filtered off with suction
  6. customtriturated with acetonitrile
  7. filtrationagain filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-aef5e39fb9be4dd1a1869ab0650cca9d
Source dataset
uspto-grants-1997_10
Patent number
US05679623

Reaction notes

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