Sodium 4-methylbenzenesulfonate → HCID 22465148, compound

HRID 1935660Notes

Reaction equation

HRID 1935660 reaction equation
S([C:5]1[CH:11]=CC(C)=[CH:7][CH:6]=1)([O-])(=O)=O.[Na+].[CH3:13][C:14]([NH2:20])([CH2:18][CH3:19])[C:15](=[S:17])[NH2:16]>CCC(C)=O>[CH2:5]([C:6]1([CH3:7])[NH:16][C:15](=[S:17])[C:14]([CH2:18][CH3:19])([CH3:13])[NH:20]1)[CH3:11]

Participants

4

Reactant 2

HCID 3720192Sodium 4-methylbenzenesulfonateHCID 22465149HCID 22465149, compound

Product 1

HCID 22465148HCID 22465148, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The thione can be purified by column chromatography on silica gel using hexane to elute an odorous fraction before the thione. The effect of variation of temperature and concentration of the reactants on yield and reaction rate was examined in a sealed NMR tube using D20 as a solvent and sodium tosylate as an internal standard. What was observed was a smooth decrease in concentration of starting materials and smooth increase in concentration of product. The reaction time can be reduced from 16 hours at 50° C. to 6 hours at 80° C. The compound, 2-methyl-2-aminobutyrothioamide, was not observed indicating that this alicyclic intermediate reacts with MEK in a fast step to yield the cyclic product

Workup

  1. customThe thione can be purified by column chromatography on silica gel
  2. washto elute an odorous fraction before the thione
  3. customThe effect of variation of temperature and concentration of the reactants on yield
  4. customreaction rate
  5. customwas examined in a sealed NMR tube
  6. temperaturesmooth increase in concentration of product
  7. customto yield the cyclic product

Sources & evidence

ORD record
ord-5132ecf3616243958efd46e0c00a155c
Source dataset
uspto-grants-2002_05
Patent number
US06388004B1

Reaction notes

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