Ethanol → HCID 18427787, compound

HRID 1871618Notes

Reaction equation

HRID 1871618 reaction equation
[Na].[O:2]1CCO[CH2:4][CH2:3]1.CS[C:10](SC)=[C:11]([C:14](=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[C:12]#[N:13].[CH2:28]([OH:30])[CH3:29]>>[CH2:3]([O:2][C:10]([O:30][CH2:28][CH3:29])=[C:11]([C:14](=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[C:12]#[N:13])[CH3:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 312751,4-DioxaneHCID 27360473,3-Bis(methylsulfanyl)-2-[3-(trifluoromethyl)benzoyl]prop-2-enenitrileHCID 5360545Sodium

Product 1

HCID 18427787HCID 18427787, compound

Procedure

Sodium (0.126 g, 5.5 mmol) was dissolved in 15 mL of ethanol and 20 mL of dioxane was added followed by 1.59 g (5.0 mmol) of 3,3-bis-methylthio-2-(3-trifluoromethylbenzoyl)-acrylonitrile and the reaction mixture was refluxed for 4 hours and let stir overnight at room temperature. This compound was relatively unstable to aqueous conditions and was not isolated as such. Instead, an aliquot of the mixture was stripped and the product was identified by 300 MHz proton NMR: NMR (DMSO-d6): 1.14 (6H, tJ=7), 3.45 (4H, q, J=7), 7.44-8.16 (4H, m).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 hours
  2. customwas not isolated as such

Sources & evidence

ORD record
ord-5594e0a42fd54bbbaffa40cbf25b7146
Source dataset
uspto-grants-2000_08
Patent number
US06103900

Reaction notes

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