Miconazole → HCID 86734174, compound

HRID 1730211Notes

Reaction equation

HRID 1730211 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.[Cl:26][C:27]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:28]=1[CH2:29]Cl>CC(C)=O>[Cl-:1].[Cl:26][C:27]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:28]=1[CH2:29][N+:8]1[CH:9]=[CH:10][N:6]([CH2:5][CH:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:3]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:2]=2[Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 4189MiconazoleHCID 72122,4-Dichlorobenzyl chloride

Product 1

HCID 86734174HCID 86734174, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15 parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)-phenethyl]imidazole and 60 parts of 2,4-dichlorobenzyl chloride are mixed together in 120 parts of acetone as solvent and the resulting mixture is stirred at reflux temperature for 40 hours. At the end of this period, the mixture is warmed to evaporate off most of the solvent and the residue is poured onto diisopropyl ether, whereupon the 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium chloride product separates as an oil. The ether is decanted off and the oily residue is washed with warm xylene and thereafter triturated in 2-propanol whereupon the oily product solidified. The solid product is filtered off, washed with 2-propanol and dried to obtain a purified product, 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride, mp. 178.9° C.

Workup

  1. temperatureat reflux temperature for 40 hours
  2. temperatureAt the end of this period, the mixture is warmed
  3. customto evaporate off most of the solvent
  4. additionthe residue is poured onto diisopropyl ether, whereupon the 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium chloride product
  5. customThe ether is decanted off
  6. washthe oily residue is washed with warm xylene
  7. customtriturated in 2-propanol whereupon the oily product
  8. filtrationThe solid product is filtered off
  9. washwashed with 2-propanol
  10. customdried

Sources & evidence

ORD record
ord-86be27dd8096446f836505ff3658a24f
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Reaction notes

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