Methyl chloroacetate → HCID 59536735, Verbindung

HRID 2402818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2402818
[CH2:1]([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Br:16])=[N:7][NH:6][C:5]1=[O:17])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][C:26]([O:28][CH3:29])=[O:27]>C(#N)C>[CH2:1]([N:4]1[C:5](=[O:17])[N:6]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[N:7]=[C:8]1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Br:16])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 59536813HCID 59536813, Verbindung

Produkt 1

HCID 59536735HCID 59536735, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Of the compound from Example 164A, 9.78 g (about 23.32 mmol, purity 75%) were dissolved in 75 ml of acetonitrile. Then 3.55 g (25.65 mmol) of potassium carbonate and 2.46 ml (27.98 mmol) of methyl chloroacetate were added. The mixture was stirred under reflux for 5 hours. After cooling, it was filtered with suction. The filtrate was concentrated a little on a rotary evaporator and then diluted with 30 ml of ethyl acetate and washed with 30 ml each of 1M hydrochloric acid and of saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. The residue was purified by chromatography on silica gel (elution: cyclohexane/ethyl acetate 2:1). This gave 7.1 g (79% of theory) of the title compound.

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. filtrationit was filtered with suction
  4. concentrationThe filtrate was concentrated a
  5. customlittle on a rotary evaporator
  6. additiondiluted with 30 ml of ethyl acetate
  7. washwashed with 30 ml each of 1M hydrochloric acid and of saturated aqueous sodium chloride solution
  8. dry with materialThe organic phase was dried over sodium sulphate
  9. filtrationfiltered
  10. customfreed from the solvent on a rotary evaporator
  11. customThe residue was purified by chromatography on silica gel (elution: cyclohexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-56e0b8281f314de080b5e66a813d5e11
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796324B2

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