Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate → Methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

HRID 349128

Reaktionsgleichung

Reaktionsgleichung von HRID 349128
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cu][C:22]#[N:23]>CN1CCCC1=O>[C:22]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:23]

Komponenten

4

Edukt 2

HCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoateHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 21086168Methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (Preparation 3) (0.15 g), copper (I) cyanide, and N-methylpyrrolidinone (1 mL) was heated at 150° C. overnight, at which time the mixture was cooled and partitioned between ethyl acetate and aq. HCl (1N). The organic layer was dried (magnesium sulfate), concentrated under reduced pressure, and the residue was chromatographed on silica gel using ethyl acetate-hexane (20/80) to give 0.066 g of the desired product. ms (m+H) 289.2. See also preparation 7 for the preparation of the acid.

Aufarbeitung

  1. temperaturewas cooled
  2. custompartitioned between ethyl acetate and aq. HCl (1N)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9f535ef1d5a1403ea013533876849b4b
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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