3,5-Dichlorophenol → HCID 178478189, compound

HRID 726261Notes

Reaction equation

HRID 726261 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([Cl:10])[CH:9]=1.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>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[O:11][CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1

Participants

6

Reactant 3

HCID 115713,5-DichlorophenolHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178478189HCID 178478189, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

288 mg (60% in oil, 7.2 mmol) of sodium hydride are added to a solution of 2.34 g (14.4 mmol) of 3,5-dichlorophenol in 4 ml of dimethylformamide while cooling in an ice bath. The mixture is stirred at room temperature for 1 hour under nitrogen. 200 mg (1.20 mmol) 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalytic amount) are then added. The mixture is heated at 80° C. for 3 days and then the solvent is evaporated under reduced pressure.

Workup

  1. temperaturewhile cooling in an ice bath
  2. temperatureThe mixture is heated at 80° C. for 3 days
  3. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-28b1266873c14caa8fa3bc00e2d2979f
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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