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

HRID 244365

Reaction equation

HRID 244365 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d886774210f642a6ad79242826ce4972
Source dataset
uspto-grants-2014_02
Patent number
US08658642B2

Linked notes

Loading…