4-Nitrophenol → HCID 178526700, compound

HRID 726252

Reaction equation

HRID 726252 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:13][CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl.C(OCC)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

9

Reactant 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178526700HCID 178526700, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

2.09 mg (1.5 mmol) of 4-nitrophenol, 251 mg (1.4 mmol) of 4-[2-chloroethyl]-1H-imidazole hydrochloride, 475 mg (3 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80° C. for 5 days in 5 ml of dimethylformamide. The reaction mixture is cooled and 100 ml of diethyl ether are added. The precipitate is separated by filtration. The filtrate is evaporated under reduced pressure to give a residue which is subjected to column chromatography (using, as first eluent, chloroform and, as second eluent, a 9/10 chloroform/methanol mixture) to give the title compound which, after crystallization from methanol, melts at: 197°-200° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe precipitate is separated by filtration
  3. customThe filtrate is evaporated under reduced pressure
  4. customto give a residue which

Sources & evidence

ORD record
ord-1b7c78a3428f4fb79d3451a9f53ebd74
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Linked notes

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