Hydroxyamine hydrochloride → HCID 178513311, compound

HRID 851995Notes

Reaction equation

HRID 851995 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl.[NH2:35][OH:36]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([NH:35][OH:36])=[NH:28])=[CH:25][CH:26]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 184551434-chloro-N-(4-cyano-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamide

Product 1

HCID 178513311HCID 178513311, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Chloro-N-(4-cyano-benzyl)-N-(2-oxo-azepan-3-yl)-benzenesulfonamide (2.09 g, 5.00 mmol), sodium bicarbonate (0.52 g, 6.15 mmol) and hydroxylamine hydrochloride (0.43 g, 6.15 mmol) in a mixture of 20 ml ethanol and 4 ml water were refluxed for 11 hours. The solvents were removed by distillation and the residue was recrystalized from water. The solid was then suspended in dichloromethane, refluxed, cooled to room temperature and filtered to yield 1.74 g (77%) 4-{[(4-chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-N-hydroxy-benzamidine as white solid, MS: m/e (%)=451.0 (MH+, 100).

Workup

  1. temperaturewere refluxed for 11 hours
  2. customThe solvents were removed by distillation
  3. customthe residue was recrystalized from water
  4. temperaturerefluxed
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3c806657716a47f083890e597ced3c06
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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