Methyl iodide → 7-chloro-9-methyl-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271083
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][CH:7]([NH:12][S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])[C:6]=2[CH:18]=1.[H-].[Na+].[CH3:22]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][CH:7]([N:12]([S:13]([CH2:16][CH3:17])(=[O:14])=[O:15])[CH3:22])[C:6]=2[CH:18]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223917937-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine

Produkt 1

HCID 223917977-chloro-9-methyl-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepineAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.6 g (2.0 mmol) of 7-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine in 8 ml of THF was added dropwise under nitrogen to a suspension of 0.1 g (2.7 mmol) of 80 percent sodium hydride in 5 ml of THF. After stirring at RT for 1 h, 0.41 g (2.9 mmol) of methyl iodide was added dropwise and the mixture was additionally stirred overnight at RT. After distilling off the solvent, the residue was treated with water and extracted with EA. After washing the organic phase with dil. hydrochloric acid and water, and drying over magnesium sulfate, it was concentrated in vacuo and the crude product was recrystallized from methylene chloride. 0.4 g of 7-chloro-9-methyl-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepine was obtained, m.p. 141-143° C.

Aufarbeitung

  1. waitthe mixture was additionally stirred overnight at RT
  2. distillationAfter distilling off the solvent
  3. additionthe residue was treated with water
  4. extractionextracted with EA
  5. washAfter washing the organic phase with dil. hydrochloric acid and water
  6. dry with materialdrying over magnesium sulfate, it
  7. concentrationwas concentrated in vacuo
  8. customthe crude product was recrystallized from methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-12cb058a26644dccb645751c439a9c93
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333349B1

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