Methyl iodide → 5-(4-Bromophenyl)-1-methyl-2-pyrrolidinone

HRID 230628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230628
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C:11](=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:12]([CH3:16])[C:11](=[O:13])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 120565955-(4-Bromophenyl)pyrrolidin-2-one

Produkt 1

HCID 577627945-(4-Bromophenyl)-1-methyl-2-pyrrolidinoneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-(4-bromophenyl)-2-pyrrolidinone (preparation described in WO00/21958) (200 mg, 0.83 mmol) in dimethylformamide (5 ml) was treated with a solid suspension of sodium hydride (60% in mineral oil, 35 mg, 0.88 mmol). The reaction mix was allowed to stir for 20 minutes, then methyl iodide (124 mg, 0.88 mmol) was added and the whole mix stirred for a further 18 hours. The reaction mixture was quenched with a few drops of water then partitioned between dichloromethane (15 ml), and water (60 ml), the organic layer was removed and washed with water again (2×10 ml), then reduced to minimum volume under reduced pressure to give the title compound as a brown oil (141 mg, 67%).

Aufarbeitung

  1. additionThe reaction mix
  2. additionthe whole mix
  3. stirringstirred for a further 18 hours
  4. customThe reaction mixture was quenched with a few drops of water
  5. customthen partitioned between dichloromethane (15 ml), and water (60 ml)
  6. customthe organic layer was removed
  7. washwashed with water again (2×10 ml)

Quellen und Nachweise

ORD-Eintrag
ord-cf2488bbaab6476fa62ce50afc52e5d1
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566735B2

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