Methane → 1-(2-Nitro-1-imidazolyl)-3-(3-bromopropylamino)-2-propanol hydrobromide

HRID 441007

반응식

HRID 441007 반응식
[Br-].[Br:2][CH2:3][CH2:4][CH2:5][NH3+:6].[OH-].[Na+].[O:9]1[CH2:20][CH:10]1[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[N+:17]([O-:19])=[O:18].C>C(O)C.C(OCC)C>[BrH:2].[N+:17]([C:13]1[N:12]([CH2:11][CH:10]([OH:9])[CH2:20][NH:6][CH2:5][CH2:4][CH2:3][Br:2])[CH:16]=[CH:15][N:14]=1)([O-:19])=[O:18]

참가 물질

7

반응물 4

HCID 297MethaneHCID 14798Sodium HydroxideHCID 3349731-(2,3-Epoxypropyl)-2-nitroimidazoleHCID 110313343-Bromopropylazanium;bromide

생성물 1

HCID 146215671-(2-Nitro-1-imidazolyl)-3-(3-bromopropylamino)-2-propanol hydrobromide수율 119.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

반응 조건

온도
20 °C

실험 절차

A solution containing 3-bromopropylammonium bromide (6.47 g, 29.6 mmol) and sodium hydroxide (1.18 g, 29.5 mmol) in ethanol (40 cm3) was stirred at 20° C.; after 1 hour, diethyl ether (40 cm3) was added and the mixture filtered. 1-(2,3-epoxypropyl)-2-nitroimidazole (5.00 g, 29.6 mmol) was added to the filtrate and the solution heated to reflux for 45 minutes. The reaction mixture was then treated with decolourising charcoal (0.5 g), filtered, concentrated under reduced pressure and treated with aqueous hydrobromic acid (48% w/w HBr, 2.0 cm3). The solid which appeared upon refrigeration was recrystallised from aqueous ethanol to give 1-(2-nitro-1-imidazolyl)-3-(3-bromopropylamino)-2-propanol hydrobromide (6.87 g, 59.9%) as a hygroscopic yellow crystalline solid.

후처리

  1. filtrationthe mixture filtered
  2. temperaturethe solution heated
  3. temperatureto reflux for 45 minutes
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additiontreated with aqueous hydrobromic acid (48% w/w HBr, 2.0 cm3)
  7. customwas recrystallised from aqueous ethanol

출처 및 근거

ORD 기록
ord-242b6d66a9ea426886a40d1965beacef
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521203

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