2-Hydroxybenzonitrile → HCID 178509671, compound

HRID 744074Notes

Reaction equation

HRID 744074 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7].Cl.Cl[CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[O:3][CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1)#[N:7]

Participants

6

Reactant 3

HCID 119072-HydroxybenzonitrileHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178509671HCID 178509671, 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 1.43 g (12 mmol) of 2-hydroxybenzonitrile 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 and the mixture is heated at 80° C. for 3 days. The solvent is evaporated under reduced pressure and the oily residue is stirred in ethanol and filtered. The filtrate is evaporated and the residue subjected to chromatography on a column of silica gel (first eluent chloroform, second eluent 95/5 chloroform/methanol). The title compound is converted to the oxalate and crystallized from an ethanol/diethyl ether (2/1) mixture, M.p.: 170°-171° C.

Workup

  1. temperaturethe mixture is heated at 80° C. for 3 days
  2. customThe solvent is evaporated under reduced pressure
  3. stirringthe oily residue is stirred in ethanol
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. customcrystallized from an ethanol/diethyl ether (2/1) mixture, M.p.: 170°-171° C.

Sources & evidence

ORD record
ord-a86d5e10324d4d66992c10833b4bbb4f
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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