Butyl iodide → 7-Chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271084ノート

反応式

HRID 2271084 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][CH:7](NS(CC)(=O)=O)[C:6]=2[CH:18]=1.[H-].[Na+].C(I)CCC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:18]=1

参加物

5

反応物 3

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

生成物 1

HCID 1317230517-Chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9eb08fdf4bc146858a7e141c29720522
出典データセット
uspto-grants-2001_12
特許番号
US06333349B1

反応ノート

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