Diethyl Sulfate → HCID 14150485, compound

HRID 2257264Notes

Reaction equation

HRID 2257264 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]N(C=O)C>>[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 6163Diethyl SulfateHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2785731,4-dihydroxynaphthalene-2,3-dicarbonitrile

Product 1

HCID 14150485HCID 14150485, compoundYield 87%

Conditions

Temperature
100 °C

Procedure

210 g (1 mol) of 1,4-dihydroxy-2,3-dicyanonaphthalene, 1 l of DMF and 339 g (2.2 mol) of diethyl sulfate were introduced at room temperature as the initial charge. 304 g (2.2 mol) of potassium carbonate were added with care. The batch was gradually heated to 100° C. and stirred at 100° C. for 6 h. It was then poured onto water and the resulting precipitate was washed with water and dried to leave 231 g of 1,4-diethoxy-2,3-dicyanonaphthalene (theory: 87% ; melting point: 167°-169° C.).

Workup

  1. additioninitial charge
  2. additionIt was then poured onto water
  3. washthe resulting precipitate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-63d6451914b44212b5e7cbabdea2b733
Source dataset
uspto-grants-1997_08
Patent number
US05656752

Reaction notes

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