Nitric Acid → 1-(5-nitro-2-thienyl)-1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]ethane

HRID 2257588ノート

反応式

HRID 2257588 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:14])[CH2:7][O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12].[C:15]([O:18]C(=O)C)(=O)[CH3:16].[N+:22]([O-])([OH:24])=[O:23].C(=O)([O-])O.[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl>[N+:22]([C:5]1[S:1][C:2]([CH:6]([O:14][C:15](=[O:18])[CH3:16])[CH2:7][O:8][CH2:9][CH2:10][N:11]([CH3:12])[CH3:13])=[CH:3][CH:4]=1)([O-:24])=[O:23]

参加物

7

反応物 5

HCID 944Nitric AcidHCID 7918Acetic Anhydride2 回HCID 14798Sodium Hydroxide2 回HCID 516892Sodium BicarbonateHCID 30766751-(2-thienyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol

生成物 1

HCID 544036141-(5-nitro-2-thienyl)-1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]ethane

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of 9.2 g of 1-(2-thienyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol and 18 ml of acetic anhydride was refluxed for 10 minutes. The reaction mixture was dropwise added to a mixture of 7.8 ml of concentrated nitric acid and 27 ml of acetic anhydride at 0° C. in 30 minutes. The resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was added to a saturated aqueous sodium hydrogen-carbonate solution with the pH of the resulting mixture having been adjusted to 7 with a 40% aqueous sodium hydroxide solution. The resulting mixture was adjusted to pH 10 with a 40% aqueous sodium hydroxide solution and 300 ml of chloroform was added thereto. The organic layer was separated and 300 ml of water was added thereto. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The aqueous layer was separated and 300 ml of chloroform was added thereto. The resulting mixture was adjusted to pH 10 with a 40% aqueous sodium hydroxide solution. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 10.4 g of oily 1-(5-nitro-2-thienyl)-1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]ethane (compound No. 404).

後処理

  1. temperaturewas refluxed for 10 minutes
  2. additionwas added
  3. customThe organic layer was separated
  4. addition300 ml of water was added
  5. customThe aqueous layer was separated
  6. addition300 ml of chloroform was added
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-2e3644de50304ba6b2bdaa700a059c3e
出典データセット
uspto-grants-1997_08
特許番号
US05658904

反応ノート

読み込み中…