Benzyl Bromide → 1-Benzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1767470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767470
[CH3:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:6]1[C:5]2[CH:12]=[CH:13][C:2]([CH3:1])=[CH:3][C:4]=2[C:9](=[O:10])[O:8][C:7]1=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2944785-Methylisatoic anhydride

Produkt 1

HCID 210819161-Benzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dioneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of Compound 11 (25 g, 141 mmol) in DMF was added slowly to a suspension of NaH (60% in mineral oil, 6.21 g, 155 mmol) in DMF and further stirred at room temperature for 1 h. Then, neat benzyl bromide (19.53 mL, 155 mmol) was added and the solution further stirred at room temperature for 3 h. The solution was poured into ice water, and the solids formed were filtered, washed several times by water, and dried. The solid was suspended in hexane, sonicated briefly, filtered, and washed by hexane to yield 36.5 g (97%) of white solids. M.P. 150° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 5.27 (s, 2H), 7.15 (d, J=8.7 Hz, 1H), 7.26–7.39 (m, 5H), 7.54 (dd, J=1.5, 8.7 Hz, 1H), 7.83 (d, J=1.5 Hz, 1H). Anal. (C16H13NO3) C, H, N.

Aufarbeitung

  1. stirringthe solution further stirred at room temperature for 3 h
  2. customthe solids formed
  3. filtrationwere filtered
  4. washwashed several times by water
  5. customdried
  6. customsonicated briefly
  7. filtrationfiltered
  8. washwashed by hexane

Quellen und Nachweise

ORD-Eintrag
ord-c2ba05575bbf4966b52cbe492f81f4d0
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235546B2

Notizen zur Reaktion

Wird geladen…