Water → HCID 19778382, compound

HRID 2082385Notes

Reaction equation

HRID 2082385 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([SH:18])[C:15]([CH3:19])=[N:14]1.[H-].[Na+].Br[C:23]1[N:24]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:25]([C:30]#[N:31])=[C:26]([C:28]#[N:29])[N:27]=1.O>O1CCCC1>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[N:17]=[C:16]([S:18][C:23]2[N:24]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:25]([C:30]#[N:31])=[C:26]([C:28]#[N:29])[N:27]=2)[C:15]([CH3:19])=[N:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 19778352HCID 19778352, compoundHCID 178433914HCID 178433914, compound

Product 1

HCID 19778382HCID 19778382, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Crude 2-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-2H-1,2,3-triazole-4-thiol, prepared as in EP 350 237, (10 g) in tetrahydrofuran (50 ml) was added to a stirred suspension of sodium hydride (80%, dispersion in oil, 1.0 g) in tetrahydrofuran (50 ml) at 0°. Then a solution of 2-bromo-4,5-dicyano-1-(2-trimethylsilylethoxymethyl)-1H-imidazole (10 g) in tetrahydrofuran (100 ml) was added, dropwise, with stirring at 0°-5°. The mixture was stirred at room temperature for 20 hours and then was poured into water and extracted with ethyl acetate. Conventional work-up and purification by column chromatography gave 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[4,5-dicyano-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-ylthio]-5-methyl-2H-1,2,3-triazole, as a pale yellow oil, nD 24°=1.526 (compound 9a).

Workup

  1. stirringThe mixture was stirred at room temperature for 20 hours
  2. extractionextracted with ethyl acetate
  3. customConventional work-up and purification by column chromatography

Sources & evidence

ORD record
ord-2937de82c2994deb99eac0d38b535011
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

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