Dimethyl Sulfoxide → HCID 12272524, compound

HRID 1727197Notes

Reaction equation

HRID 1727197 reaction equation
CS(C)=O.CC1C=CC(S([CH2:15][N+:16]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](=O)[CH3:31]>[Cl-].[Na+].O.CCCCCC.C(OCC)(=O)C.CO>[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]([CH3:31])[C:15]#[N:16]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 142862-AcetylpyridineHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 12272524HCID 12272524, compoundYield 192.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 131727289HCID 131727289, compoundSolvent

Procedure

To a dried flask under nitrogen was added dimethyl sulphoxide (100 ml) and tosmic (20.95 g, 107.3 mmol). The reaction mixture was cooled to 0° C. before potassium t-butoxide (33.35° g, 297.1 mmol) was added. After 5 min, methanol (3.7 ml) was added followed by 1-(2-pyridinyl)ethanone (10 g, 32.5 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured in brine:hexane:ethyl acetate (50:25:25). The organic extracts were dried (Na2SO4) and concentrated in vacuo to yield a crude oil. The oil was purified by flash chromatography eluting with ethyl acetate:hexane (3:7) to give the title compound as a brown solid (8.26 g, 76%).

Workup

  1. additionwas added
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto yield a crude oil
  5. customThe oil was purified by flash chromatography
  6. washeluting with ethyl acetate:hexane (3:7)

Sources & evidence

ORD record
ord-d907116df9674614a53b572f2cd4a8fd
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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