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

HRID 52167노트

반응식

HRID 52167 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-624ca4af81174a03af47f19059b5a6e5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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