Sodium ethoxide → HCID 57856475, compound

HRID 19664Notes

Reaction equation

HRID 19664 reaction equation
Cl.[C:2](=[NH:9])([NH2:8])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[O-]CC.[Na+].C(O[CH:17]=[CH:18][C:19](=O)[C:20]([F:23])([F:22])[F:21])C>C(O)C>[CH2:3]([C:2]1[N:8]=[C:19]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:17][N:9]=1)[CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-oneHCID 552849605-Hexenimidamide hydrochloride

Product 1

HCID 57856475HCID 57856475, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-hexenimidamide hydrochloride (P4, 200 mg) in ethanol (1.8 mL), sodium ethoxide (92 mg) was added and the mixture stirred at r.t. for 5 min. 4-(Ethyloxy)-1,1,1-trifluoro-3-buten-2-one (0.13 mL) was then added and the mixture was stirred at room temperature for 18 h. The solvent was evaporated, the residue was dissolved in dichloromethane and the organic layer was washed with H2O and dried over Na2SO4. This solution was filtered and the filtrate was concentrated in vacuo. The crude was purified by column chromatography (eluting with dichloromethane/methanol 95/5) to give 143 mg of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washthe organic layer was washed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationThis solution was filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe crude was purified by column chromatography (eluting with dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-d2a43fb2d0ef40cda6030776f1895c05
Source dataset
uspto-grants-2010_06
Patent number
US07745458B2

Reaction notes

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