Phenyl chloroformate → N,O-Bis-(phenoxycarbonyl)-hydroxylamine

HRID 413575

반응식

HRID 413575 반응식
[C:1](=[O:4])([OH:3])[O-].[Na+].Cl.[NH2:7][OH:8].[C:9]1([O:15][C:16](Cl)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[O:3]([C:1]([NH:7][O:8][C:16]([O:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17])=[O:4])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 15891Phenyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate2회

생성물 1

HCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamine수율 68%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a solution of sodium bicarbonate (21.5 g, 0.256 mol) in water (150 ml) at 0° C. was added hydroxylamine hydrochloride (8.8 g, 0.127 mol). The reaction mixture was tirred for 30 min. and phenylchloroformate (60 g, 0.383 mol) was introduced directly into the vigorously stirred mixture. Sodium bicarbonate (32.3 g, 3.85 mol) in water (300 ml) was added to the mixture. The mixture was stirred for 30 min., the ice-bath removed and stirring continued for an additional 2 h at room temperature. The resultant suspension was filtered and the filter cake washed with water. The wet filter cake was collected, suspended in hexane, filtered and again washed with hexane. The solid was kept at 0° C. overnight to afford N,O-bis-phenoxycarbonylhydroxylamine (23.5 g, 68%) as a solid. Melting point: 80-82° C. 1H NMR (CDCl3, 200 MHz): δ 7.26(m, 5H), 7.42 (m, 5H) and 8.54 (s, 1H).

후처리

  1. customthe ice-bath removed
  2. stirringstirring
  3. waitcontinued for an additional 2 h at room temperature
  4. filtrationThe resultant suspension was filtered
  5. washthe filter cake washed with water
  6. customThe wet filter cake was collected
  7. filtrationfiltered
  8. washagain washed with hexane
  9. waitThe solid was kept at 0° C. overnight

출처 및 근거

ORD 기록
ord-f4e30f4bede849dfb005ba3725dbd292
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566538B1

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