N-bromobutanimide → Tert-butyl 1-bromo-6-cyano-2-naphthylcarbamate

HRID 2238393

Reaktionsgleichung

Reaktionsgleichung von HRID 2238393
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6]2)#[N:2].C1C(=O)N([Br:28])C(=O)C1>CC#N>[Br:28][C:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 44549529Tert-butyl 6-cyano-2-naphthylcarbamate

Produkt 1

HCID 44549797Tert-butyl 1-bromo-6-cyano-2-naphthylcarbamateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 140 (4.48 g, 18 mmol) and NBS (3.85 g, 21.6 mmol) in MeCN (80 mL) was stirred at reflux for 1 h, then concentrated under reduced pressure. The residue was dissolved in CH2Cl2, washed with 10% aqueous Na2SO3, water, dried, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2Cl2, to give tert-butyl 1-bromo-6-cyano-2-naphthylcarbamate (141) (5.69 g, 91%): mp (iPr2O/hexane) 164-166° C.; 1H NMR [(CD3)2SO] δ 9.01 (s, 1H), 8.63 (d, J=1.5 Hz, 1H), 8.27 (d, J=9.0 Hz, 1H), 8.07 (d, J=9.0 Hz, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.93 (dd, J=8.9, 1.8 Hz, 1H), 1.50 (s, 9H). Anal. (C16H15BrN2O2) C, H, N, Br.

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with 10% aqueous Na2SO3, water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-12d9edc40d124302aacf6517a7cc2406
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718688B2

Verknüpfte Notizen

Wird geladen…