1,3-dihydro-4-methyl-2H-imidazol-2-one → HCID 12856029, compound

HRID 1995718Notes

Reaction equation

HRID 1995718 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1.Cl.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCC(Cl)(Cl)Cl>[C:9]([C:6]1[NH:5][C:4](=[O:7])[NH:3][C:2]=1[CH3:1])(=[O:16])[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 6451240Aluminum(III) ChlorideHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 12856029HCID 12856029, compound

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

In 80 ml tetrachloroethane are placed 3.87 g (39.5 mmole) 1,3-dihydro-4-methyl-2H-imidazole-2-one and 7 g (39.5 mmole) isonicotinoyl chloride hydrochloride. Aluminum chloride (26 g, 194 mmole) is added and the mixture is stirred at 85° C. for 3 hours. The tetrachloroethane is decanted from the reaction mixture and the residue is quenched with water and neutralized with sodium bicarbonate. The suspension is filtered and the filtrate evaporated to dryness. Chromatography over silica gel affords the title compound; m.p. 295°-96°.

Workup

  1. customThe tetrachloroethane is decanted from the reaction mixture
  2. customthe residue is quenched with water and neutralized with sodium bicarbonate
  3. filtrationThe suspension is filtered
  4. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-9d15da9ca5f94417a671004e4970add4
Source dataset
uspto-grants-1983_09
Patent number
US04405628

Reaction notes

Loading…