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

HRID 52167ノート

反応式

HRID 52167 の反応式
[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>[OH:11][N:10]([CH:21]([C:23]#[CH:24])[CH3:22])[C:8]([NH2:26])=[O:1]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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-hydroxy-N-(3-butyn-2-yl)urea (340 mg, 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.

後処理

  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

出典と根拠

ORDレコード
ord-624ca4af81174a03af47f19059b5a6e5
出典データセット
uspto-grants-1997_04
特許番号
US05616596

反応ノート

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