Hydrochloric Acid → 4-(3,5-dichlorophenoxy)-3-{[2-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinyl]sulfonyl}benzonitrile hydrochloride

HRID 2242818Notes

Reaction equation

HRID 2242818 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:31][C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=2)=[C:7]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH:13]2[CH2:25][N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)(=[O:11])=[O:10])[CH:8]=1)#[N:2].Cl>C(Cl)Cl.O1CCOCC1>[ClH:38].[Cl:39][C:34]1[CH:33]=[C:32]([CH:37]=[C:36]([Cl:38])[CH:35]=1)[O:31][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][C:7]=1[S:9]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH:13]1[CH2:25][N:26]1[CH:30]=[N:29][CH:28]=[N:27]1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59208297tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy) phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate

Product 1

HCID 685223234-(3,5-dichlorophenoxy)-3-{[2-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinyl]sulfonyl}benzonitrile hydrochlorideYield 179.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-{[5-cyano-2-(3,5-dichlorophenoxy) phenyl]sulfonyl}-3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate (37 mg, 0.06 mmol) in CH2Cl2 (1 ml) was added 4N HCl in 1,4-dioxane (1 ml). The mixture was stirred for 2 hours at room temperature. The solvent was evaporated in vacuo, the residue was triturated with Et2O and the white solid was collected by filtration to give 4-(3,5-dichlorophenoxy)-3-{[2-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinyl]sulfonyl}benzonitrile hydrochloride (28.5 mg, 86.3%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was triturated with Et2O
  3. filtrationthe white solid was collected by filtration

Sources & evidence

ORD record
ord-16dff6658d8a42a2b021ddd826a690e1
Source dataset
uspto-grants-2010_03
Patent number
US07674797B2

Reaction notes

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