Diethyl Sulfate → HCID 15457414, compound

HRID 650691Notes

Reaction equation

HRID 650691 reaction equation
[CH:1]([C:3]1[NH:4][C:5]([C:10]#[N:11])=[C:6]([C:8]#[N:9])[N:7]=1)=[CH2:2].[CH2:12](N(CC)CC)[CH3:13].S(OCC)(OCC)(=O)=O>C(OCC)(=O)C.C1COCC1.CCCCCC.C(OCC)(=O)C>[CH2:12]([N:7]1[C:6]([C:8]#[N:9])=[C:5]([C:10]#[N:11])[N:4]=[C:3]1[CH:1]=[CH2:2])[CH3:13]

Participants

7

Reactant 3

HCID 6163Diethyl SulfateHCID 8471TriethylamineHCID 121131612-Ethenyl-1H-imidazole-4,5-dicarbonitrile

Product 1

HCID 15457414HCID 15457414, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A flask equipped with a magnetic stirbar was charged with 6.26 g of 2-vinyldicyanoimidazole. To this, 75 ml of distilled THF and 6.1 ml of triethylamine were added with stirring. After 5 minutes stirring, 5.7 ml of diethyl sulphate was added. This mixture was allowed to stir for 2 days. Analysis by TLC (50/50 hexane/ethyl acetate, UV visualization) showed the reaction was complete (starting material rf 0.3, product rf 0.6). The THF solution was rotovapped and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with 10% aqueous sodium hydroxide. The combined aqueous layers were back extracted with methylene chloride. The combined organic layers were dried with magnesium sulphate and rotovapped to dryness. The crude residue was triturated with ether. The ether extracts were rotovapped and the residue recrystallized with ether/hexanes to yield 3.124 g of the product, mp 66-70° C. as yellow needles. A second crop yielded 1.72 g for a combined yield of 65%.

Workup

  1. customA flask equipped with a magnetic stirbar
  2. stirringAfter 5 minutes stirring
  3. stirringto stir for 2 days
  4. washThe ethyl acetate was washed with 10% aqueous sodium hydroxide
  5. extractionThe combined aqueous layers were back extracted with methylene chloride
  6. dry with materialThe combined organic layers were dried with magnesium sulphate
  7. customThe crude residue was triturated with ether
  8. customthe residue recrystallized with ether/hexanes

Sources & evidence

ORD record
ord-b6a9ba8c731542138225e70a6a28ef4f
Source dataset
uspto-grants-2001_08
Patent number
US06274724B1

Reaction notes

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