Miconazole → HCID 178478169, compound

HRID 328646Notes

Reaction equation

HRID 328646 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH:4]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[Br:26][C:27]1[CH:36]=[CH:35][C:30]([O:31][CH2:32][CH2:33]Br)=[CH:29][CH:28]=1>C(#N)C>[Br-:26].[Br:26][C:27]1[CH:36]=[CH:35][C:30]([O:31][CH2:32][CH2:33][N+:8]2[CH:9]=[CH:10][N:6]([CH2:5][CH:4]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[C:3]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:2]=3[Cl:1])[CH:7]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 4189MiconazoleHCID 877972-Bromoethyl p-bromophenyl ether

Product 1

HCID 178478169HCID 178478169, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.2 parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazole, 3.1 parts of 2-(p-bromophenoxy)ethyl bromide and 24 parts of acetonitrile are stirred together overnight at reflux temperature to obtain the desired 1-[2-(p -bromophenoxy)ethyl]-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium bromide product. The product is recovered from the reaction mixture by (a) diluting the latter with diisopropyl ether (b) adding three drops of water to precipitate the product as a crystalline solid, and (c) filtering off the precipitated solid. After purification by recrystallization from a mixture of 4-methyl-2-pentanone and diisopropyl ether, the product has a melting point of 131.5°-132.5° C.

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-499d67db08f84dffa72670934e4667d1
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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