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Hydroxylamine HCl → Diethyl 2,2'-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate

HRID 68319
Notes
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Reaction equation

HRID 68319 reaction equation
[C:1]([C:4]1[O:8][C:7]([N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[Na+].[Cl-].[OH:28][NH3+:29]>C(O)C.O>[OH:28][N:29]=[C:1]([C:4]1[O:8][C:7]([N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:5]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 68282007Diethyl 2,2'-((5-acetyloxazol-2-yl)azanediyl)diacetate

Product 1

HCID 86699627Diethyl 2,2'-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetateYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

Procedure

To a solution of diethyl 2,2′-((5-acetyloxazol-2-yl)azanediyl)diacetate (300 mg, 1.01 mmoles) in ethanol (6 mL), a solution of sodium acetate (165 mg, 2.01 mmoles) and hydroxylammonium chloride (139 mg gm, 2.01 mmoles) in water (2 ml) was added and the reaction mixture was refluxed for 1 h. The reaction mixture was cooled to room temperature and solvent was evapourated in vacuum. The residue was diluted with ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure to yield 252 mg (80%) of title product as thick liquid.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. additionThe residue was diluted with ice cold water
  3. extractionextracted with ethyl acetate
  4. extractionThe combined ethyl acetate extract
  5. washwas washed with water & brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-408cfd8f82b84c36a51f220cd42224fb
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822414B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes