Miconazole → HCID 86734177, compound

HRID 328645Notes

Reaction equation

HRID 328645 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][CH:27]([CH3:39])[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)=[O:29]>C(#N)C>[Br-:26].[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:27]([C:28](=[O:29])[NH:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=2)[CH3:39])[CH:7]=1

Participants

4

Reactant 2

HCID 4189MiconazoleHCID 21443167HCID 21443167, compound

Product 1

HCID 86734177HCID 86734177, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8 parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazole, 5.6 parts of 2-bromo-N-(p-methylbenzyl)propionamide and 80 parts of acetonitrile is stirred and refluxed for 20 hours. The reaction mixture is evaporated and the residue is crystallized from a mixture of 4-methyl-2-pentanone and diisopropyl ether, yielding 9 parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-{1-[N-(p-methylbenzyl)carbamoyl]ethyl}-imidazolium bromide; mp. 136.2° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is crystallized from a mixture of 4-methyl-2-pentanone and diisopropyl ether

Sources & evidence

ORD record
ord-faf0065d2ee4497bbe0095164fc905cc
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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