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1,2-Dibromoethane → 1-Benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene

HRID 1939612
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1939612
[OH-].[K+].Cl.[NH2:4]O.[CH2:6]([S:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].BrCCBr>CO>[CH2:6]([S:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]1[O:18][CH2:19][CH2:24][O:27][N:4]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 775668Benzoic acid, 2-[(phenylmethyl)thio]-, methyl ester

Produkt 1

HCID 221041471-Benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene
Ausbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

160 g (2.86 mol) of potassium hydroxide in 700 ml of methanol are added dropwise, at room temperature, to a mixture of 98.7 g (1.42 mol) of hydroxylamine hydrochloride and 700 ml of methanol. Subsequently, 184 g (0.712 mol) of methyl 2-(benzylthio)benzoate are added in portions at room temperature. The mixture is stirred at 40° C. overnight. 98.1 g (0.712 mol) of potassium carbonate are then added, 601 g (3.20 mol) of 1,2-dibromoethane are added dropwise, and the mixture is left stirring at 60° C. overnight. Subsequently, the solvent is distilled off under reduced pressure. The residue is partitioned between methylene chloride and water. The organic phase is dried and the solvent is distilled off under reduced pressure. The residue is stirred up with absolute ethyl alcohol. The solid is filtered off with suction and dried under high vacuum. 43.1 g (21% of theory) of 1-benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene are obtained as a pale yellow solid. Melting point: 73°-77° C.

Aufarbeitung

  1. waitthe mixture is left
  2. stirringstirring at 60° C. overnight
  3. distillationSubsequently, the solvent is distilled off under reduced pressure
  4. customThe residue is partitioned between methylene chloride and water
  5. customThe organic phase is dried
  6. distillationthe solvent is distilled off under reduced pressure
  7. stirringThe residue is stirred up with absolute ethyl alcohol
  8. filtrationThe solid is filtered off with suction
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-100118ea4d22424ebc442eb03511fc14
Quelldatensatz
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05696257

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