Hydroxyamine hydrochloride → HCID 72315998, compound

HRID 385745Notes

Reaction equation

HRID 385745 reaction equation
[N+:1]([C:4]1[S:5][C:6]([C:11]2[N:15]=[CH:14][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:12]=2)=[CH:7][C:8]=1[CH:9]=O)([O-:3])=[O:2].[NH2:24][OH:25].Cl.CC([O-])=O.[Na+]>CCO.C([O-])(O)=O.[Na+]>[N+:1]([C:4]1[S:5][C:6]([C:11]2[N:15]=[CH:14][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:12]=2)=[CH:7][C:8]=1[CH:9]=[N:24][OH:25])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 59525931HCID 59525931, compound

Product 1

HCID 72315998HCID 72315998, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Nitro-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)thiophene-3-carbaldehyde (1.85 g, 5.22 mmol), NH2OH.HCl (381 mg, 5.48 mmol), and NaOAc (450 mg, 5.48 mmol) were combined in EtOH (30 mL) and stirred at room temperature for 2 h. The reaction was diluted with saturated NaHCO3 and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound as an orange solid (mixture of oxime E/Z isomers).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bd5d04096eda41f283551a73b61815e2
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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