Hydroxyamine hydrochloride → HCID 178428486, compound

HRID 1059878Notes

Reaction equation

HRID 1059878 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH3:9][C:10]1[N:11]=[C:12]([NH:22][C:23](=[NH:27])SCC)[S:13][C:14]=1[C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=1>CC(O)C.C(OCC)(=O)C>[CH3:9][C:10]1[N:11]=[C:12]([NH:22][C:23]([NH:2][OH:3])=[NH:27])[S:13][C:14]=1[C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178477486HCID 178477486, compound

Product 1

HCID 178428486HCID 178428486, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of hydroxylamine hydrochloride (146 mg) and sodium acetate (172 mg) in 2-propanol (4 ml) was added N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)-S-ethylisothiourea (205 mg), and the mixture was stirred at 90° C. for 1 hour. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, 3 to 4% methanol in dichloromethane) to give N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)-N′-hydroxyguanidine (81 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel, 3 to 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e76a9efe167a432fa12634e234f663d8
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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