Sodium hydride → 4-Fluorobenzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 346585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346585
[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+].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>CN(C=O)C>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[C:5]3[CH:12]=[CH:13][C:2]([CH3:1])=[CH:3][C:4]=3[C:9](=[O:10])[O:8][C:7]2=[O:11])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 2944785-Methylisatoic anhydride

Produkt 1

HCID 865946424-Fluorobenzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dioneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of Compound 11 (5 g, 28 mmol) in DMF was added slowly to a suspension of NaH (60% in mineral oil, 1.24 g, 31 mmol) in DMF and further stirred at room temperature for 1 h. Then, neat 4-fluorobenzyl bromide (3.81 mL, 31 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 solids were suspended in hexane, sonicated briefly, filtered, and washed by hexane to yield 6.3 g (79%) of white solids. M.P. 153° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 5.24 (s, 2H), 7.14–7.17 (m, 3H), 7.44 (m, 2H), 7.54 (dd, J=1.7, 8.2 Hz, 1H), 7.83 (d, J=1.2 Hz, 1H). Anal. (C16H12FNO3) 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-64048d0233c443eaa08149699e05cae3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173036B2

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