Benzenesulfonyl chloride, 4-chloro-3-nitro- → 1-[(4-Chloro-3-nitrophenyl)sulfonyl]-4-methylpiperazine

HRID 72764

反応式

HRID 72764 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29]>O1CCCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29]

参加物

5

反応物 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine

生成物 1

HCID 28424191-[(4-Chloro-3-nitrophenyl)sulfonyl]-4-methylpiperazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

N-methylpiperazine 3.6 mL, N,N-diisopropylethylamine 5.7 mL and tetrahydrofuran 31 mL were mixed and dropped into a solution of 4-chloro-3-nitrobenzenesulfonyl chloride 8.19 g in tetrahydrofuran 51 mL, under cooling with ice, followed by stirring for 30 minutes under cooling with ice. The stirring was then continued for 17 hours at room temperature. The solvent was distilled off and the residue was poured in water, of which pH was raised to 9 with saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate-tetrahydrofuran mixed solvent. The organic layer was washed with saturated brine, dried over magnesium sulfate, and from which the solvent was distilled off. Recrystallizing the crude product from ethyl acetate-hexane mixed solvent, 4.29 g of the title compound was obtained.

後処理

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. waitThe stirring was then continued for 17 hours at room temperature
  4. distillationThe solvent was distilled off
  5. additionthe residue was poured in water, of which pH
  6. temperaturewas raised to 9 with saturated aqueous sodium hydrogencarbonate solution
  7. extractionfollowed by extraction with ethyl acetate-tetrahydrofuran mixed solvent
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. distillationfrom which the solvent was distilled off
  11. customRecrystallizing the crude product from ethyl acetate-hexane mixed solvent

出典と根拠

ORDレコード
ord-4d91e65e5fd44d5796f1e47c01e6fcd9
出典データセット
uspto-grants-2014_09
特許番号
US08829000B2

関連ノート

読み込み中…