Diethyl (ethoxymethylene)malonate → 651755-15-6

HRID 485682Notes

Reaction equation

HRID 485682 reaction equation
[CH2:1]([NH:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC[O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O>[CH2:1]([N:8]1[C:19](=[O:18])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11157(Phenylmethyl)hydrazineHCID 11430Potassium Carbonate

Product 1

HCID 353972651755-15-6

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl hydrazine (324 mg, 2.65 mmol) in water (15 ml) containing potassium carbonate (368 mg, 2.65 mmol) was treated with diethyl ethoxymethylene malonate (575 μl, 2.65 mmol) and the whole refluxed for 3 hours. The reaction mixture was allowed to cool and then washed with ethyl acetate. The aqueous solution was then acidified (HCl) to pH 2 and extracted with ethyl acetate. The ethyl acetate extraction was dried (MgSO4) and evaporated to give the title product as an oily solid which solidified on hexane trituration 265 mg, 41%), recrystallised from aqueous ethanol, mp 79°-81° C. νmax (CHCl3) 1720, 1659, 1575 cm-1. δ(CDCl3) 1.37 (3H, t, J8 Hz, --OCH2CH3), 4.4 (2H, q, J8 Hz, OCH2CH3), 5.23 (2H, s, --CH2N), 7.44 (5H, m, phenyl protons), 7.73 (1H, s, C3 pyrazole proton), 8.50 (1H, bs, --NH proton). Found: M+, 246.0995; C13H14N2O3 requires M, 246.1003.

Workup

  1. temperaturethe whole refluxed for 3 hours
  2. temperatureto cool
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extraction
  6. dry with materialwas dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-8569583c894c44299876bf62a418c07a
Source dataset
uspto-grants-1985_08
Patent number
US04537886

Reaction notes

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