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

HRID 1184383

反応式

HRID 1184383 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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, Rf=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 147 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).

後処理

  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

出典と根拠

ORDレコード
ord-dea719c9ef9144cfaa178f71bab02f77
出典データセット
uspto-grants-2014_03
特許番号
US08669247B2

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