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

HRID 2271083ノート

反応式

HRID 2271083 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]([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

参加物

5

反応物 3

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

生成物 1

HCID 223917977-chloro-9-methyl-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepine収率 62.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

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 and water
  6. dry with materialdrying over magnesium sulfate, it
  7. concentrationwas concentrated in vacuo
  8. customthe crude product was recrystallized from methylene chloride

出典と根拠

ORDレコード
ord-12cb058a26644dccb645751c439a9c93
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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