Miconazole → Fludazonium chloride

HRID 1730210

Reaction equation

HRID 1730210 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[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)=[O:29]>C(Cl)Cl>[Cl-:1].[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]([CH2:27][C:28](=[O:29])[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4189MiconazoleHCID 1202482-Chloro-4'-fluoroacetophenone

Product 1

HCID 178521219Fludazonium chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to that previously described, 4.2 parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazole, 1.7 parts of 2-chloro-4'-fluoroacetophenone and 40 parts of methylene chloride are mixed together and stirred at reflux temperature for 15 hours. Thereafter, the solvent is evaporated under reduced pressure and the residue triturated in 4-methyl-2-pentanone. The solid is recovered by filtration and crystallized from acetonitrile to obtain a purified 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-fluorobenzoylmethyl)-imidazolium chloride product, mp. 181° C.

Workup

  1. temperatureat reflux temperature for 15 hours
  2. customThereafter, the solvent is evaporated under reduced pressure
  3. customthe residue triturated in 4-methyl-2-pentanone
  4. filtrationThe solid is recovered by filtration
  5. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-e94936bb18474fdb94e445d1e546c37b
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Linked notes

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