Hydrochloric Acid → 1-(2-(2,5-Dichlorophenoxy)-5-nitrophenylsulfonyl)piperazine

HRID 244365

반응식

HRID 244365 반응식
[Cl:1][C:2]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:14]([N:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)(=[O:16])=[O:15].Cl.CCOC(C)=O>C(Cl)Cl.O1CCOCC1>[Cl:1][C:2]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(=[O:16])=[O:15]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 66770240Tert-butyl 4-(2-(2,5-dichlorophenoxy)-5-nitrophenylsulfonyl)piperazine-1-carboxylate

생성물 1

HCID 592608601-(2-(2,5-Dichlorophenoxy)-5-nitrophenylsulfonyl)piperazine수율 97.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of compound 39 (0.100 g, 0.19 mmol) in DCM (6.00 mL) was added 1N HCl in 1,4-dioxane (0.570 mL). The reaction was monitored with TLC (25% EtOAc in hexanes, Rt=0.0). The reaction was complete after stirring at room temperature for 16 hrs, as indicated by the absence of the starting material). The reaction mixture was concentrated and the residual was redissolved in MeOH (2.00 mL). Et2O (4.00 mL) was then added and the mixture was stirred until precipitate formed (10 min). The solid was collected by filtration to yield compound 40 as a white solid (0.080 g, 100% HPLC purity, 83% yield). 1H NMR (500 MHz, DMSO-d6): δ 9.39 (s, 2H), 8.61 (d, J=2 Hz, 1H), 8.45 (dd, J1=3 Hz, J2=9 Hz, 1H), 7.78 (d, J=9 Hz, 1H), 7.73 (d, J=2 Hz, 1H), 7.53 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 3.57 (m, 4H), 3.16 (m, 4H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residual was redissolved in MeOH (2.00 mL)
  3. additionEt2O (4.00 mL) was then added
  4. stirringthe mixture was stirred until precipitate
  5. customformed (10 min)
  6. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-d886774210f642a6ad79242826ce4972
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658642B2

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