Dimethyl Sulfoxide → HCID 59478041, compound

HRID 1516568Notes

Reaction equation

HRID 1516568 reaction equation
[H-].[Na+].C1(C)C=CC(S([CH:12]([N+:14]#[C-])C)(=O)=O)=CC=1.[C:17](#[N:24])[CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH3:23].CS(C)=O.[CH2:29](OCC)[CH3:30]>O>[CH2:20]([C:19]1[C:18]([C:12]#[N:14])=[CH:17][NH:24][C:29]=1[CH3:30])[CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 287344HCID 287344, compoundHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 59478041HCID 59478041, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of sodium hydride (60%, 0.096 g) in diethyl ether (3 mL) were added a solution of 1-(toluene-4-sulfonyl)ethylisocyanide (0.42 g) and 2-heptenenitrile (0.22 g) in a mixed solvent of diethyl ether (3 mL) and dimethylsulfoxide (3 mL) at room temperature, and this mixture was stirred at room temperature for 1 hour. To this reaction mixture was added water (15 mL). This mixture was extracted with ethyl acetate, and this organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (0.19 g).

Workup

  1. extractionThis mixture was extracted with ethyl acetate
  2. washthis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-1419d716f859426dbde32ab5b3b90fe2
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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