Hydroxyamine hydrochloride → HCID 178426664, compound

HRID 245093Notes

Reaction equation

HRID 245093 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[Cl:9][C:10]1[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[C:12]([CH3:18])[C:11]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21]>CO>[Cl:9][C:10]1[CH:15]=[C:14]([CH:13]=[C:12]([CH3:18])[C:11]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:16]([NH:2][OH:3])=[NH:17]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67491342N-(2-chloro-4-cyano-6-methyl-phenyl)-methanesulfonamide

Product 1

HCID 178426664HCID 178426664, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Hydroxylamine hydrochloride (60 mg, 858 μmol) and NaHCO3 (72 mg, 858 μmol) is added to a solution of N-(2-chloro-4-cyano-6-methyl-phenyl)-methanesulfonamide (105 mg, 429 μmol) in methanol (10 mL). The mixture is stirred at 65° C. for 18 h. The solvent is removed in vacuo and the residue is dissolved in a small volume of water (2 mL) and extracted three times with EA (15 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give the title compound (118 mg) as a white solid; LC-MS**: tR=0.19 min, [M+1]+=277.94; 1H NMR (CDCl3): δ2.57 (s, 3H), 3.13 (s, 3H), 6.21 (s, 1H), 7.49 (d, J=1.5 Hz, 1H), 7.63 (d, J=1.5 Hz).

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in a small volume of water (2 mL)
  3. extractionextracted three times with EA (15 mL)
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-a5477cb57aff457e9db86d30e2adf600
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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