Cyclohexene → HCID 86612999, compound

HRID 2235545Notes

Reaction equation

HRID 2235545 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:5]([NH:6][CH3:7])=[C:4]([N+:13]([O-])=O)[CH:3]=1.C1CCCCC=1.C(=O)([O-])[O-].[Na+].[Na+].[N:28]([C:31]1[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][C:32]=1[CH3:39])=[C:29]=[S:30]>C(O)C.[Pd]>[NH2:10][C:8]1[C:5]([NH:6][CH3:7])=[C:4]([NH:13][C:29]([NH:28][C:31]2[C:32]([CH3:39])=[CH:33][C:34]([CH3:38])=[CH:35][C:36]=2[CH3:37])=[S:30])[CH:3]=[C:2]([F:1])[CH:9]=1

Participants

7

Reactant 4

HCID 8079CyclohexeneHCID 10340Sodium CarbonateHCID 1386592,4,6-Trimethylphenyl isothiocyanateHCID 86020358HCID 86020358, compound

Product 1

HCID 86612999HCID 86612999, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 75 mL of ethanol was mixed 1.30 g (6.04 mmol) of 4-fluoro-N-methyl-2,6-dinitroaniline, 3.7 mL (36 mmol) of cyclohexene and 5.1 g (2.4 mmol, 40 mol %) of 10% palladium on carbon (50% water, Degussa type). The mixture was refluxed for 2.5 h and filtered into a flask containing 0.77 g (7.3 mmol) of sodium carbonate and 1.07 g (6.04 mmol) of 2-isothiocyanato-1,3,5-trimethylbenzene. The resulting slurry was refluxed for 4 h, concentrated and slurried in dichloromethane. The slurry was filtered, concentrated and purified by flash chromatography eluting with a 70% hexanes/ethyl acetate mixture to give 0.65 g (32%) of the title compound as an off-white solid.

Workup

  1. temperatureThe mixture was refluxed for 2.5 h
  2. filtrationfiltered into a flask
  3. temperatureThe resulting slurry was refluxed for 4 h
  4. concentrationconcentrated
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated
  7. custompurified by flash chromatography
  8. washeluting with a 70% hexanes/ethyl acetate mixture

Sources & evidence

ORD record
ord-d565cc4c438c406eb2e9a9d30e32598b
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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