Ammonium Hydroxide → N-hydroxy-N-(butyn-2-yl)urea

HRID 1720439

Reaction equation

HRID 1720439 reaction equation
[O:1]([C:8]([N:10]([CH:21]([C:23]#[CH:24])[CH3:22])[O:11]C(OC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.[OH-].[NH4+:26]>CO>[CH3:22][CH:21]([N:10]([OH:11])[C:8]([NH2:26])=[O:1])[C:23]#[CH:24]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 19963272N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine

Product 1

HCID 19963264N-hydroxy-N-(butyn-2-yl)ureaYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N,O-Bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine (3.14 g,9.7 mmol), methanol (20 mL), and ammonium hydroxide (20 mL) was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic solution was washed with brine, dried over MgSO4, filtered, and concentrated. Chromatography on silica gel (2% methanol, methylene chloride) afforded N-(3-butyn-2-yl)N-hydroxyurea (340 rag, 28%). 1H NMR (DMSO-26, 300 MHz) δ1.25 (d, 3H, J=7.5 Hz), 3.05 (d, 1H, J=3.0 Hz), 4.85 (dq, 1H, J=7.5, 3.0 Hz), 6.50 (br s, 1H), 9.25 (S, 1H). MS (DCI/NH3) m/e 129 (M+H)+, 146 (M+NH4)+. Anal calcd for C5H8N2O2 : C, 46.87; H, 6.29; N, 21.86. Found: C, 47.03; H, 6.27; N, 21.98.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e17450f3f3404879a73ba26d07b30cd3
Source dataset
uspto-grants-1996_04
Patent number
US05506261

Linked notes

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