1-Naphthol → HCID 178419980, compound

HRID 744076Notes

Reaction equation

HRID 744076 reaction equation
[H-].[Na+].[C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl.Cl[CH2:16][CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:3]1([O:13][CH2:16][CH2:17][C:18]2[N:19]=[CH:20][NH:21][CH:22]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 70051-NaphtholHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178419980HCID 178419980, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

240 mg (60% in oil, 6 mmol) of sodium hydride are added to a solution of 1.73 g (12 mmol) of 1-naphthol in 10 ml of dimethylformamide. The mixture is stirred at room temperature for 1 hour under nitrogen. 200 mg (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalytic amount) are added. The mixture is heated at 100° C. for 3 days and the solvent is then evaporated under reduced pressure. The remaining oily residue is taken up in dichloromethane and an aqueous sodium carbonate solution and treated with active charcoal. The dichloromethane solution is separated and evaporated and the remaining residue is chromatographed on a column of silica gel (10/1 dichloromethane/methanol) to give the title compound in the base form. The oxalate is prepared from isopropanol and is crystallized from ethanol, M.p.: 187°-189° C.

Workup

  1. temperatureThe mixture is heated at 100° C. for 3 days
  2. customthe solvent is then evaporated under reduced pressure
  3. additionan aqueous sodium carbonate solution and treated with active charcoal
  4. customThe dichloromethane solution is separated
  5. customevaporated
  6. customthe remaining residue is chromatographed on a column of silica gel (10/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-38a9540c29f14a5aab25df2fe58c3c06
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

Loading…