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

HRID 72764

반응식

HRID 72764 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d91e65e5fd44d5796f1e47c01e6fcd9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829000B2

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