Potassium Carbonate → HCID 86650547, compound

HRID 2172177Notes

Reaction equation

HRID 2172177 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F-].[Cs+].[Cl:9][C:10]1[NH:11][CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[N:14]=1.[CH3:18][C:19]1([CH2:22][CH2:23]OS(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:21][O:20]1>O.CN(C=O)C>[Cl:9][C:10]1[N:11]([CH2:23][CH2:22][C:19]2([CH3:18])[CH2:21][O:20]2)[CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[N:14]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 86709365HCID 86709365, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 86650547HCID 86650547, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (1.16 g) and cesium fluoride (196 mg) were added to a DMF solution (20 ml) of 2-chloro-4-nitro-1H-imidazole (953 mg) and 4-nitrobenzene sulfonic acid 2-(2-methyloxiranyl)ethyl ester (1.856 g), and the mixture was stirred at 60° C. overnight. Thereafter the reaction mixture was cooled to room temperature. Water was added to the reaction solution, and the reaction mixture was then extracted repeatedly with ethyl acetate. The combined organic layer was washed with water and a saturated sodium chloride aqueous solution, and then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1) to afford the title compound as a yellow oil (1.1 g).

Workup

  1. temperatureThereafter the reaction mixture was cooled to room temperature
  2. extractionthe reaction mixture was then extracted repeatedly with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and then dried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-5cf7bd5cfa9c4fa0bd366feab7872bf2
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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