Hydroxyamine hydrochloride → HCID 178513365, compound

HRID 2172690Notes

Reaction equation

HRID 2172690 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][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].C(=O)(O)[O-].[Na+].[NH2:24][OH:25].Cl>CCO.CCOC(C)=O.O>[OH:25][NH:24][C:1](=[NH:2])[C:3]1[CH:8]=[CH:7][C:6]([S:9](=[O:11])(=[O:10])[NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 7033676HCID 7033676, compound

Product 1

HCID 178513365HCID 178513365, compoundYield 87.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-Cyano-N-phenyl-benzenesulfonamide (crude) (198 mg, 0.652 mmol), Sodium bicarbonate (547 mg, 6.52 mmol) and NH2OH.HCl (453 mg, 6.52 mmol) was dissolved in EtOH (2172 μL) and the resulting solution stirred overnight at 60° C. The mixture was diluted with EtOAc and water. The water phase was extracted and the combined organic phases washed with brine, then dried over magnesium sulfate. After evaporation of the solvent, 175 mg (0.571 mmol) of a white solid was obtained. The product was used without purification in the next step.

Workup

  1. extractionThe water phase was extracted
  2. washthe combined organic phases washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-97dddab300fa464f91599a1928816c7a
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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