3-Cyanophenol → HCID 178509864, compound

HRID 1387179Notes

Reaction equation

HRID 1387179 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].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:7]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=1)[O:3][CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1)#[N:8]

Participants

6

Reactant 3

HCID 133943-CyanophenolHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178509864HCID 178509864, 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 3-hydroxybenzonitrile in 10 ml of dimethylformamide and 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 for 3 hours at 80° C. The solvent is evaporated under reduced pressure and the oily residue is stirred in ethanol and filtered. The filtrate is evaporated and the residue is purified by 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 a 2/1 ethanol/diethyl ether mixture, M.p.: 189°-190° C.

Workup

  1. temperaturethe mixture is heated for 3 hours at 80° C
  2. customThe solvent is evaporated under reduced pressure
  3. stirringthe oily residue is stirred in ethanol
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. customthe residue is purified by chromatography on a column of silica gel (first eluent chloroform, second eluent 95/5 chloroform/methanol)
  7. customcrystallized from a 2/1 ethanol/diethyl ether mixture, M.p.: 189°-190° C.

Sources & evidence

ORD record
ord-616fb85179ba435188cac3aa7149162a
Source dataset
uspto-grants-2001_07
Patent number
USRE037303E1

Reaction notes

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