Miconazole → Fludazonium chloride

HRID 328639

Reaction equation

HRID 328639 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-dichloroβ-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-fluorobenzoylmethyl)imidazolium chloride product, m.p. 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-98e3ef4685bc4e8fb9ab499c88062115
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Linked notes

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