Dimethyl Sulfate → HCID 14150496, compound

HRID 2257262Notes

Reaction equation

HRID 2257262 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](O)=[C:4]([C:13]#[N:14])[C:3]=1[C:15]#[N:16].S([O:22][CH3:23])(OC)(=O)=O.[C:24](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:24][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:22][CH3:23])=[C:4]([C:13]#[N:14])[C:3]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2785731,4-dihydroxynaphthalene-2,3-dicarbonitrile

Product 1

HCID 14150496HCID 14150496, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

42 g (0.2 mol) of 1,4-dihydroxy-2,3-dicyanonaphthalene and 200 ml of N,N-dimethylformamide (DMF) were introduced at room temperature as the initial charge. 55.4 g (0.44 mol) of dimethyl sulfate and 60.8 g (0.44 mol) of potassium carbonate were added. The batch was slowly heated to 100° C. and stirred at that temperature for 8 h. It was then poured onto water, and the resulting precipitate was filtered off with suction, washed With water and dried to leave 30 g of 1,4-dimethoxy-2,3-dicyanonaphthalene (theory: 64%; melting point: 190° C.).

Workup

  1. additioninitial charge
  2. additionIt was then poured onto water
  3. filtrationthe resulting precipitate was filtered off with suction
  4. washwashed With water
  5. customdried

Sources & evidence

ORD record
ord-b694fa1d9ce84648b7b4b6811aa593cd
Source dataset
uspto-grants-1997_08
Patent number
US05656752

Reaction notes

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