Hydroxyamine hydrochloride → 4-amino-N-hydroxy-6-(methyl-3-methylphenyl-amino)-[1,3,5]triazine-2-carboxamidine

HRID 341464Notes

Reaction equation

HRID 341464 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]#[N:17])[N:3]=1.Cl.[NH2:19][OH:20].[C:21](=O)([O-])O.[Na+]>CCO.O>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:21])[CH:10]=2)[N:5]=[C:4]([C:16]([NH:19][OH:20])=[NH:17])[N:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 668029964-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazine-2-carbonitrile2×

Product 1

HCID 1784255374-amino-N-hydroxy-6-(methyl-3-methylphenyl-amino)-[1,3,5]triazine-2-carboxamidineYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-amino-6-(methyl-phenyl-amino)-[1,3,5]triazine-2-carbonitrile (Intermediate 2, 138 mg, 0.6 mmol) in EtOH (4 mL) was added to a solution of hydroxylamine hydrochloride (51 mg, 0.7 mmol) and sodium hydrogencarbonate (61 mg, 0.73 mmol) in water (2 mL). The mixture was heated at 70 C for 2 h, allowed to cool to room temperature and the solvent evaporated. The crude solid residue was slurried with water (4 mL) before filtering under reduced pressure to afford Intermediate 1 (95 mg, 60%). Method C HPLC-MS: MH+ requires m/z=260. Found: m/z=260, Rt=0.88 min (98%).

Workup

  1. temperatureThe mixture was heated at 70 C for 2 h
  2. customthe solvent evaporated
  3. filtrationbefore filtering under reduced pressure

Sources & evidence

ORD record
ord-e777cd5cb78b45ac80b2b331a1dd5cc4
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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