Hydroxyamine hydrochloride → 3-[tert-butyl(diphenyl)silyl]oxy-N'-hydroxypropanimidamide

HRID 385961Notes

Reaction equation

HRID 385961 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]#[N:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].C(=O)(O)[O-].[Na+]>CO>[Si:1]([O:18][CH2:19][CH2:20]/[C:21](=[N:24]/[OH:25])/[NH2:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 108287163-(Tert-butyldiphenylsilyloxy)propanenitrile

Product 1

HCID 108548133-[tert-butyl(diphenyl)silyl]oxy-N'-hydroxypropanimidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-{[tert-butyl(diphenyl)silyl]oxy}propanenitrile (4.4 g, 14.2 mmol) in methanol (40 ml) was added hydroxylamine hydrochloride (8.9 g, 128 mmol) and sodium bicarbonate (11.9 g, 142 mmol). The mixture was heated at reflux for 48 hours. The mixture was then cooled to room temperature, the solvent was evaporated, ice water was added, and the resulting solution was extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (50-100% ethyl acetate in hexanes) to afford the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 hours
  3. customthe solvent was evaporated
  4. additionice water was added
  5. extractionthe resulting solution was extracted with ethyl acetate (2×)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified via silica gel chromatography (50-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-77cdbc2d4af54a2d857c8ebed1a6ced4
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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