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Triethylamine → [6-(2-Bromoacetyl)-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide

HRID 1295946
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Reaktionsgleichung

Reaktionsgleichung von HRID 1295946
C(N(CC)CC)C.[C:8]([C:11]1[CH:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]#[N:22])[C:15]=2[CH:23]=1)(=[O:10])[CH3:9].[Br:28]N1C(=O)CCC1=O.C(OCC)(=O)C>O1CCCC1>[Br:28][CH2:9][C:8]([C:11]1[CH:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]#[N:22])[C:15]=2[CH:23]=1)=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 22930164(6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide

Produkt 1

HCID 58910016[6-(2-Bromoacetyl)-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (0.76 ml, 5.5 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (0.73 g, 5.5 mmol) were added to a solution of [6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide (0.5 g, 1.8 mmol) in tetrahydrofuran (50 ml) while cooling on ice and the mixture was stirred at the same temperature for 30 minutes, after which N-bromosuccinimide (0.49 g, 2.7 mmol) was added and stirring was continued for 30 minutes. Ethyl acetate was added, the reaction mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (310 mg) as a light yellow solid.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. washthe reaction mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4f65d0c3f2bb419db040afc4f4d8c07f
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07244730B2

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