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

HRID 1072214노트

반응식

HRID 1072214 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 223918015-(N-butyl-N-ethylsulfonylamino)-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine수율 96.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-03cc466ed2114e68a93549e62448102d
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908947B2

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