Sodium Bicarbonate → (2Z)-3-Amino-2-cyano-4-ethyl-2-hexene

HRID 2262448Notes

Reaction equation

HRID 2262448 reaction equation
[NH2:1]/[C:2](/[CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[C:3](/[C:7]#[N:8])\[C:4](Cl)=O.C([O-])(O)=O.[Na+]>C(#N)C.O>[NH2:1]/[C:2](/[CH:9]([CH2:10][CH3:11])[CH2:12][CH3:13])=[C:3](\[C:7]#[N:8])/[CH3:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86595835(2Z)-3-Amino-2-cyano-4-ethyl-2-hexenoyl chloride

Product 1

HCID 86595836(2Z)-3-Amino-2-cyano-4-ethyl-2-hexeneYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

3 g (15 mmol) of (2Z)-3-amino-2-cyano-4-ethyl-2-hexenoyl chloride dissolved in acetonitrile were added dropwise to a solution of 2.6 g (30 mmol) NaHCO3 in water. The solution was stirred at 25° C. for 30 min, then concentrated to dryness and the residue was taken up in methanol. The precipitate was seperated and the filtrate concencentrated to dryness again. The residue was dissolved in water and saturated KHSO4-solution was added. Filtration of the precipitate gave 2 g of the title compound (73% of theory) as a colorless solid (m. p. 150° C.)

Workup

  1. concentrationconcentrated to dryness
  2. customThe precipitate was seperated
  3. dissolutionThe residue was dissolved in water
  4. additionsaturated KHSO4-solution was added
  5. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-12016601758e4ca2949e51d73b61092e
Source dataset
uspto-grants-2010_12
Patent number
US07851411B2

Reaction notes

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