Butyl iodide → 5-(N-butyl-N-ethylsulfonylamino)-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

HRID 1072214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072214
[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+].[CH2:22](I)[CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:22]([N:12]([CH:7]1[C:6]2[CH:18]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:19])[C:5]=2[O:11][CH2:10][CH2:9][CH2:8]1)[S:13]([CH2:16][CH3:17])(=[O:14])=[O:15])[CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 223917937-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine

Produkt 1

HCID 223918015-(N-butyl-N-ethylsulfonylamino)-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepineAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 0.8 g (2.6 mmol) of 7-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine (Example 10c) in 10 ml of DMF was added dropwise under nitrogen to a suspension of 0.1 g (2.7 mmol) of 80 percent sodium hydride in 8 ml of DMF. After stirring at RT for 30 min, 0.68 g (3.7 mmol) of butyl 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 in water, and drying over magnesium sulfate, it was concentrated in vacuo. 0.9 g of 5-(N-butyl-N-ethylsulfonylamino)-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine was obtained, m.p. 83-87° 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 in water
  6. dry with materialdrying over magnesium sulfate, it
  7. concentrationwas concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-03cc466ed2114e68a93549e62448102d
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908947B2

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