Hydrochloric Acid → HCID 178526855, compound

HRID 1158300Notes

Reaction equation

HRID 1158300 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[Cl:9][C:10]1[NH:11][CH:12]=[CH:13][N:14]=1.C(=O)([O-])O.[Na+].Cl>[N+](C)([O-])=O>[Cl:9][C:10]1[NH:11][CH:12]=[C:13]([N+:7]([O-:8])=[O:6])[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 27733282-chloro-1H-imidazoleHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 178526855HCID 178526855, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Nitronium tetrafluoroborate (398 mg) was dissolved in nitromethane (5 ml), next 2-chloroimidazole (205 mg) was added, the reaction mixture was stirred at a room temperature for 1 hour. The reaction mixture was neutralized with an aqueous solution of sodium hydrogencarbonate, then was turned back to acidic by adding hydrochloric acid, the separated 2-chloro-4-nitroimidazole (137 mg) was collected by filtration. The filtrate was extracted with ethyl acetate-methanol, the solid matter obtained from the organic layer was triturated with diethyl ether, 2-chloro-4-nitroimidazole (103 mg) was obtained. The sum of 240 mg (yield: 81.3%) of 2-chloro-4-nitroimidazole was obtained as colorless solid product. 1H-NMR (DMSO-d6) δ(ppm): 8.44 (1H, s), 14.19 (1H, bs).

Workup

  1. filtrationthe separated 2-chloro-4-nitroimidazole (137 mg) was collected by filtration
  2. extractionThe filtrate was extracted with ethyl acetate-methanol
  3. customthe solid matter obtained from the organic layer
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-ba8ead7fc46942f0af06a55ea0653e5c
Source dataset
uspto-grants-2010_10
Patent number
US07807843B2

Reaction notes

Loading…