Iodoethane → HCID 67041773, compound

HRID 908211Notes

Reaction equation

HRID 908211 reaction equation
[Na].[CH2:2]([O:4][C:5]([C:7]1[NH:8][N:9]=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6])[CH3:3].[CH2:17](I)[CH3:18]>C(O)C.C([O-])C.[Na+]>[CH2:2]([O:4][C:5]([C:7]1[N:8]([CH2:17][CH3:18])[N:9]=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 5360545SodiumHCID 145056993,4-diethyl 1H-pyrazole-3,4-dicarboxylate

Product 1

HCID 67041773HCID 67041773, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent2×

Procedure

Sodium ethanolate solution was freshly prepared by dissolving sodium (240 mg) in ethanol (30 ml). 2H-Pyrazole-3,4-dicarboxylic acid diethyl ester (800 mg, 3.77 mmol) was dissolved in this sodium ethanolate solution (11 ml) and stirred for 10 min (r.t.), before ethyl iodide (1.4 g, 9 mmol) was added dropwise. After the completion of the addition, the mixture was heated to reflux until all starting material was consumed (1 h). The solvent was then evaporated, the residue was taken up in ethyl acetate and washed (water). The organic layer was dried (Na2SO4), evaporated, and the title compound (280 mg, 31%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). (The regioisomeric 1-ethyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester can also be isolated, and can be distinguished from the desired product by NOE-1H-NMR.) MS (m/e)=241.1 [M+H+].

Workup

  1. additionAfter the completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux until all starting material
  4. customwas consumed (1 h)
  5. customThe solvent was then evaporated
  6. washwashed (water)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-0c7ea9105d0d42d4b01389033485e101
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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