Dimethyl Sulfoxide → HCID 59478041, compound

HRID 570821Notes

Reaction equation

HRID 570821 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-82461a7798fd4b4a9a52befd31b019e3
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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