Sodium hydride → Tioconazole

HRID 1265342Notes

Reaction equation

HRID 1265342 reaction equation
[H-].[Na+:2].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH:11]([OH:18])[CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.[Cl:19][C:20]1[S:21][CH:22]=[CH:23][C:24]=1[CH2:25][Br:26]>C1CCCCC1.C(O)(C)C>[CH:7]1[C:8]([Cl:10])=[CH:9][C:4]([Cl:3])=[C:5]([CH:11]([O:18][CH2:25][C:24]2[CH:23]=[CH:22][S:21][C:20]=2[Cl:19])[CH2:12][N:13]2[CH:14]=[N:15][CH:16]=[CH:17]2)[CH:6]=1.[Br-:26].[Na+:2]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 109327473-(Bromomethyl)-2-chlorothiophene

Product 2

HCID 5482TioconazoleHCID 253881Sodium Bromide

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8078CyclohexaneSolvent2×

Procedure

Step B of example 3 was repeated with the following exceptions: NaH (about 6.4 g), cyclohexane (about 75.6 g), 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol (about 41.2 g), and isopropanol (228 g) were employed. The cyclohexane solution of 2-chloro-3-bromomethylthiophene was then added to the reactor containing the imidazoyl mixture and the contents stirred at reflux for 4 hours, yielding a solution of crude tioconazole and solid sodium bromide. Processing continued in accordance with example 3. The crude reaction yield is ca. 25.3% based on 2-chloro-3-methylthiophene.

Workup

  1. temperatureat reflux for 4 hours

Sources & evidence

ORD record
ord-306aa5f2e24445979b6056ebb9209248
Source dataset
uspto-grants-2003_04
Patent number
US06545163B1

Reaction notes

Loading…