Ethanol → 2-Ethenylquinoxaline

HRID 456599

Reaction equation

HRID 456599 reaction equation
S(OC)(OC)(=O)=O.[N:8]1S[N:11]=[C:10]2[CH:13]=[C:14](CC#N)[CH:15]=[CH:16][C:9]=12.C(N([CH2:25][CH3:26])CC)C.[CH2:27](O)[CH3:28]>O>[CH:27]([C:25]1[CH:26]=[N:8][C:9]2[C:10](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)=[CH2:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 695224455-Cyanomethylbenz-2,1,3-thiadiazole

Product 1

HCID 218034212-EthenylquinoxalineYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl sulfate (1.07 ml, 11.3 mmol) was added dropwise, while maintaining the mixture temperature below 40° C., to a solution of amine (a) (2.6 g 11.3 mmol) in ethanol (3 ml). The thick mixture was diluted with water (15 ml) then triethylamine (1.13 ml) was added and the mixture heated for 2 hours on a water bath. After cooling the mixture was extracted with diethyl ether. The organic phase was dried over magnesium sulfate, concentrated to dryness and the residue was chromatographed on silica eluting with heptane-ethyl acetate (3-1) to give the product (1.16 g, 66%).

Workup

  1. temperaturewhile maintaining the mixture temperature below 40° C.
  2. temperaturethe mixture heated for 2 hours on a water bath
  3. temperatureAfter cooling the mixture
  4. extractionwas extracted with diethyl ether
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customthe residue was chromatographed on silica eluting with heptane-ethyl acetate (3-1)

Sources & evidence

ORD record
ord-3a2816ff52c14b7685cc57f5e516a080
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Linked notes

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