Diethyl Ether → HCID 178419398, compound

HRID 726260Notes

Reaction equation

HRID 726260 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl.Cl[CH2:13][CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1.C(OCC)C>C(N)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 78084-BromophenolHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178419398HCID 178419398, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 713FormamideSolvent

Procedure

240 mg (60% in oil; 6 mmol) of sodium hydride are slowly added to a solution of 2.07 g (12 mmol) of 4-bromophenol in 10 ml of formamide and the mixture is stirred at room temperature for 1 hour. 200 mg (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalyst) are added and the mixture is stirred at 80° C for 3 days. The reaction mixture is cooled and 150 ml of diethyl ether are added. The precipitate is separated by filtration and the filtrate is evaporated under reduced pressure to give a residue which is subjected to column chromatography through silica gel (first eluent ethyl acetate and second eluent 95/5 ethyl acetate/methanol). The title compound is purified by preparative high performance chromatography and then converted to the oxalate which, after crystallization from an ethanol/diethyl ether mixture, melts at 162°-165° C.

Workup

  1. stirringthe mixture is stirred at 80° C for 3 days
  2. temperatureThe reaction mixture is cooled
  3. customThe precipitate is separated by filtration
  4. customthe filtrate is evaporated under reduced pressure
  5. customto give a residue which
  6. customThe title compound is purified by preparative high performance chromatography
  7. customafter crystallization from an ethanol/diethyl ether mixture, melts at 162°-165° C.

Sources & evidence

ORD record
ord-0e57f98f284d4c02831a42013f4a65c1
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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