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

HRID 441007ノート

反応式

HRID 441007 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-242b6d66a9ea426886a40d1965beacef
出典データセット
uspto-grants-1996_05
特許番号
US05521203

反応ノート

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