Hydroxyamine hydrochloride → HCID 178424389, compound

HRID 2172693Notes

Reaction equation

HRID 2172693 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:21][OH:22].C(=O)([O-])O.[Na+]>C(O)C>[OH:22][NH:21][C:1](=[NH:2])[C:3]1[CH:8]=[CH:7][C:6]([S:9](=[O:10])(=[O:11])[NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 7235814HCID 7235814, compound

Product 1

HCID 178424389HCID 178424389, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-cyano-N-o-tolyl-benzenesulfonamide (214 mg, 0.629 mmol) in ethanol (3 mL), hydroxylamine hydrochloride (437 mg, 6.29 mmol) and sodium hydrogen carbonate (528 mg, 6.29 mmol) were added and the resulting suspension was stirred at 60° C. for 18 hrs. Subsequently the reaction mixture was filtered. The precipitate was washed with ethanol and the combined eluents were evaporated under reduced pressure. The residue was dried under high vacuum (45° C., 3 hrs) to give N-hydroxy-4-o-tolylsulfamoyl-benzamidine (345 mg, 0.56 mmol, 89% crude yield, purity 49.6%) as beige solid.

Workup

  1. filtrationSubsequently the reaction mixture was filtered
  2. washThe precipitate was washed with ethanol
  3. customthe combined eluents were evaporated under reduced pressure
  4. customThe residue was dried under high vacuum (45° C., 3 hrs)

Sources & evidence

ORD record
ord-b124efefe4d34f9685683a68cc0bf5f8
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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