4-Hydroxybenzophenone → HCID 178519479, compound

HRID 744077Notes

Reaction equation

HRID 744077 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1.Cl.Cl[CH2:20][CH2:21][C:22]1[N:23]=[CH:24][NH:25][CH:26]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:20][CH2:21][C:22]2[N:23]=[CH:24][NH:25][CH:26]=2)=[CH:17][CH:16]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 143474-HydroxybenzophenoneHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178519479HCID 178519479, 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 2.34 g (12 mmol) of 4-hydroxybenzophenone 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 then added. The mixture is heated at 100° C. for 2 days and the solvent is then evaporated under reduced pressure. Dilute hydrochloric acid is added to the oily residue and the excess hydroxybenzophenone is extracted with diethyl ether. The aqueous solution is basified with potassium carbonate and the product is extracted with diethyl ether. The title compound is converted to the dioxalate. Crystallization from an ethanol/diethyl ether (2/1) mixture gives a pure product, M.p.: 193°-194° C.

Workup

  1. temperatureThe mixture is heated at 100° C. for 2 days
  2. customthe solvent is then evaporated under reduced pressure
  3. additionDilute hydrochloric acid is added to the oily residue
  4. extractionthe excess hydroxybenzophenone is extracted with diethyl ether
  5. extractionthe product is extracted with diethyl ether
  6. customCrystallization from an ethanol/diethyl ether (2/1) mixture
  7. customgives a pure product, M.p.: 193°-194° C.

Sources & evidence

ORD record
ord-69464914ed3742409d3d2ae17133c353
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

Loading…