Imidazole → HCID 86745239, compound

HRID 974278Notes

Reaction equation

HRID 974278 reaction equation
[NH+]1C=CC=CC=1.[CH3:7][O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[Cl:24])[C:15]([C:25]([O:27][CH3:28])=[O:26])=[C:14]([CH3:29])[NH:13][C:12]=1[CH3:30])=[O:10].[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH:16]1[C:15]([C:25]([O:27][CH3:28])=[O:26])=[C:14]([CH3:29])[NH:13][C:12]([CH2:30][C:32]2[NH:31][CH:35]=[CH:34][N:33]=2)=[C:11]1[C:9]([O:8][CH3:7])=[O:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 24436Sodium SulfateHCID 3378865Dimethyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 4989215Pyridinium

Product 1

HCID 86745239HCID 86745239, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridinium perbromide hydrobromide (5.6 g, 17.5 mmol) was added to a stirred ice-cooled solution of 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid dimethylester (5.55 g, 15 mmol) and pyridine (2 g) in methylene dichloride (80ml). The solution was stirred at ice temperature for 40 minutes then washed with ice cold water (1×100 ml). The organic phase was separated and imidazole (6.8 g, 0.1 mol) added followed by anhydrous Na2SO4. After drying for 20 minutes the solution was filtered to remove NaSO4, evaporated and the residue heated on a steam bath for 40 minutes. The residue was then dissolved in EtOAc, washed with water (2×50 ml), dried, evaporated and crystallised from methyl acetate (15 ml) to give the crystalline title compound (3.34 g). This was suspended in isopropyl alcohol/methyl acetate (2:3 v/v)and acidified with ethanolic HCl to give the hydrochloride salt on cooling, m.p. 167°-170° C.

Workup

  1. washthen washed with ice cold water (1×100 ml)
  2. customThe organic phase was separated
  3. customAfter drying for 20 minutes the solution
  4. filtrationwas filtered
  5. customto remove NaSO4
  6. customevaporated
  7. temperaturethe residue heated on a steam bath for 40 minutes
  8. dissolutionThe residue was then dissolved in EtOAc
  9. washwashed with water (2×50 ml)
  10. customdried
  11. customevaporated
  12. customcrystallised from methyl acetate (15 ml)

Sources & evidence

ORD record
ord-77e6d84ab3c94d4996696449bca17cc6
Source dataset
uspto-grants-1991_11
Patent number
US05068337

Reaction notes

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