Nicotinic Acid → HCID 70170044, compound

HRID 2230068Notes

Reaction equation

[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:14][C:15]1[N:19](CCO)[C:18]([N+:23]([O-:25])=[O:24])=[CH:17][N:16]=1>>[CH3:14][C:15]1[NH:19][C:18]([N+:23]([O-:25])=[O:24])=[CH:17][N:16]=1.[C:1]([O:9][CH2:14][CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

Reactant 3

HCID 938Nicotinic Acid

HCID 4173Metronidazole

HCID 24386Thionyl Chloride

Product 1

HCID 70170044HCID 70170044, compoundYield 171.5%

Conditions

Temperature: 70 °C

Procedure

The reaction mixture of nicotinic acid (1.23 g, 10 mmol) and thionyl chloride (3 ml) was refluxed for 2 h, the excessive thionyl chloride was evaporated under vacuum. The residue was dissolved in 5 ml of pyridine. To this solution, metronidazole (1.20 g, 7.0 mmol) was added. The mixture was stirred at 70° C. for 2 h. Pyridine was then removed under reduced pressure. The residue was dissolved in dichloromethane. The organic layer of CH2Cl2 was washed with saturated aqueous NaHCO3 solution, water, and brine, and then dried over MgSO4. The solvent was removed. The resulting pale yellow solid was recrystallized from ethyl alcohol to give 1.67 g (86.72%) 2-methyl-5-nitro-1H-imidazole-1-ethyl nicotinate. m.p.: 116-118° C.

Workup

temperaturewas refluxed for 2 h
customthe excessive thionyl chloride was evaporated under vacuum
dissolutionThe residue was dissolved in 5 ml of pyridine
customPyridine was then removed under reduced pressure
dissolutionThe residue was dissolved in dichloromethane
washThe organic layer of CH2Cl2 was washed with saturated aqueous NaHCO3 solution, water, and brine
dry with materialdried over MgSO4
customThe solvent was removed
customThe resulting pale yellow solid was recrystallized from ethyl alcohol

Sources & evidence

ORD record: ord-9d7b7c030e5d45118cb290816a20c59f
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423707B1

Reaction notes

Loading…