1,2-Ethanedithiol → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(2-methyl-1,3-dithiolane-2-yl)-4-methylthio-1H-pyrazole

HRID 1106687Notes

Reaction equation

HRID 1106687 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](=O)[CH3:20])[C:3]=1[S:22][CH3:23].[CH2:24]([SH:27])[CH2:25][SH:26]>[Fe](Cl)(Cl)Cl.C(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]2([CH3:20])[S:27][CH2:24][CH2:25][S:26]2)[C:3]=1[S:22][CH3:23]

Participants

5

Reactant 2

HCID 109021,2-EthanedithiolHCID 117839363-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole

Product 1

HCID 224612025-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-(2-methyl-1,3-dithiolane-2-yl)-4-methylthio-1H-pyrazoleYield 8.4%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1 g (2.60 mmol) of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-acetyl-4-methylthio-1H-pyrazole, 0.26 ml (3.10 mmol) of 1,2-ethanedithiol, 0.084 g (0.5 mmol) of iron(III) chloride and 25 ml of methylene chloride was stirred at 20° C. under an inert atmosphere for 6 days. The mixture was evaporated and chromatographed so as to give 100 mg of yellow oil of the title compound. Mass spectral analysis gave a molecular weight of 460.

Workup

  1. customThe mixture was evaporated
  2. customchromatographed so as

Sources & evidence

ORD record
ord-1a3145e2073449b0b28170b104e77517
Source dataset
uspto-grants-2000_05
Patent number
US06057354

Reaction notes

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