Diethyl Ether → HCID 178435926, compound

HRID 430672Notes

Reaction equation

HRID 430672 reaction equation
C[CH2:2][O:3][CH2:4][CH3:5].[CH2:6]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([NH:12][NH2:13])=O)[CH3:7]>C(#N)C>[CH2:6]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]1[N:12]=[C:10]([C:9]2[CH:8]=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:14]=2)[NH:13][N:12]=1)[CH3:7]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 131336082-Ethylbenzohydrazide

Product 1

HCID 178435926HCID 178435926, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of immino ether (85 mg, 0.474 mmoles) and 2-ethyl benzo-hydrazide (164 mg, 1 mmole) in acetonitrile (0.5 mL), was warmed under reflux. After 1 hour stirring, solvent was distilled and substituted by 2-ethoxyethanol (0.6 mL). The reaction mixture was refluxed for 3 hours, the solvent evaporated under vacuum and the residue, re-dissolved in CH2Cl2 (2 mL), was chromatographed on a silica gel column (10 g). As elution solvents, mixtures of CH2Cl2 and CH3COOC2H5 in varying proportion (99:1 to 95:5) were used. Fractions containing the desired product were collected, solvent evaporated to give 96,27 mg (72.6%) of compound (XIII). Of particular interest, was compound (XIV), which, can be synthesised according to the procedure hereafter reported in example 2.

Workup

  1. temperaturewas warmed
  2. temperatureunder reflux
  3. distillationsolvent was distilled
  4. temperatureThe reaction mixture was refluxed for 3 hours
  5. customthe solvent evaporated under vacuum
  6. dissolutionthe residue, re-dissolved in CH2Cl2 (2 mL)
  7. customwas chromatographed on a silica gel column (10 g)
  8. washAs elution solvents, mixtures of CH2Cl2 and CH3COOC2H5
  9. additionFractions containing the desired product
  10. customwere collected
  11. customsolvent evaporated

Sources & evidence

ORD record
ord-b15d7ecfd8af41b291fc77d076d55eef
Source dataset
uspto-grants-2001_11
Patent number
US06323230B1

Reaction notes

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