Hydroxyamine hydrochloride → Benzyl N-allyl-N-[2-hydroxyiminoethyl]carbamate

HRID 470210Notes

Reaction equation

HRID 470210 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]=O)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].Cl.[NH2:19][OH:20].O.O.O.C([O-])(=O)C.[Na+]>C(#N)C.O>[CH2:1]([N:4]([CH2:15][CH:16]=[N:19][OH:20])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 57415664Benzyl allyl(2-oxoethyl)carbamate

Product 1

HCID 74074414Benzyl N-allyl-N-[2-hydroxyiminoethyl]carbamateYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of benzyl N-allyl-N-(2-oxoethyl)carbamate (25 g, 107 mmol) in acetonitrile (150 mL) is treated with hydroxylamine hydrochloride (9.68 g, 139 mmol) and a solution of sodium acetate trihydrate (16 g, 117.9 mmol) in water (75 mL). The mixture is stirred at room temperature overnight. The acetonitrile is evaporated and the aqueous solution is extracted with ethyl acetate. The organic layer is separated, dried over magnesium sulfate, and concentrated under vacuum to give the title compound (24 g, 90%). ES/MS (m/e): 249 (M+H).

Workup

  1. customThe acetonitrile is evaporated
  2. extractionthe aqueous solution is extracted with ethyl acetate
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8728c2f4ec114a13948e04d973488b34
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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