Isopropanol → Tioconazole

HRID 1265340Notes

Reaction equation

HRID 1265340 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[OH-].[Na+:18].C(O)(C)C.[Cl:23][C:24]1[S:25][CH:26]=[CH:27][C:28]=1[CH2:29][Br:30]>C1CCCCC1>[CH:5]1[C:6]([Cl:8])=[CH:7][C:2]([Cl:1])=[C:3]([CH:9]([O:16][CH2:29][C:28]2[CH:27]=[CH:26][S:25][C:24]=2[Cl:23])[CH2:10][N:11]2[CH:12]=[N:13][CH:14]=[CH:15]2)[CH:4]=1.[Br-:30].[Na+:18]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 109327473-(Bromomethyl)-2-chlorothiophene

Product 2

HCID 5482TioconazoleHCID 253881Sodium Bromide

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

(Step B) A second reactor was charged with about 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol (about 102.9 g), sodium hydroxide pellets (about 15.7 g) and isopropanol (about 384.1 g). The contents were stirred and refluxed for about three hours. After cooling to room temperature, the cyclohexane solution of 2-chloro-3-bromomethylthiophene of step A was added to the reactor and the contents stirred overnight yielding a solution of crude tioconazole and solid sodium bromide. Water (about 75.7 g) was added to the reaction mixture to dissolve the solids. The crude reaction yield was ca. 49% based on 2-chloro-3-methylthiophene.

Workup

  1. temperaturerefluxed for about three hours
  2. stirringthe contents stirred overnight

Sources & evidence

ORD record
ord-19105a530a5440019bb58322de60223f
Source dataset
uspto-grants-2003_04
Patent number
US06545163B1

Reaction notes

Loading…