Dimethyl Sulfoxide → HCID 14150485, compound

HRID 2257263Notes

Reaction equation

HRID 2257263 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]#[N:14])[C:3]=1[C:15]#[N:16].S(OCC)(O[CH2:21][CH3:22])(=O)=O.[C:26](=[O:29])([O-])[O-].[K+].[K+].[CH3:32]S(C)=O>>[CH2:21]([O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:29][CH2:26][CH3:32])=[C:3]([C:15]#[N:16])[C:4]=1[C:13]#[N:14])[CH3:22]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 2785731,4-dihydroxynaphthalene-2,3-dicarbonitrile

Product 1

HCID 14150485HCID 14150485, compoundYield 87%

Procedure

21 g (0.1 mol) of 1,4-dihydroxy-2,3-dicyanonaphthalene, 100 ml of dimethyl sulfoxide and 38.5 g (0.25 mol) of diethyl sulfate were introduced at room temperature as the initial charge. 38.6 g (0.28 mol) of potassium carbonate were added with stirring. The batch was then stirred at 100° C. for 10 h and thereafter poured onto ice-water, and the resulting precipitate was washed with water and dried to leave 23.3 g of 1,4-diethoxy-2,3-dicyanonaphthalene (theory: 87%; melting point: 167° C.).

Workup

  1. additioninitial charge
  2. stirringThe batch was then stirred at 100° C. for 10 h
  3. additionpoured onto ice-water
  4. washthe resulting precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-b1c162bf9d074f9bb43707123dfb415b
Source dataset
uspto-grants-1997_08
Patent number
US05656752

Reaction notes

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