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

HRID 976553노트

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HRID 976553 반응식
[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]

참가 물질

7

반응물 5

HCID 944Nitric AcidHCID 7918Acetic Anhydride2회HCID 14798Sodium Hydroxide2회HCID 516892Sodium BicarbonateHCID 30766751-(2-thienyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4727dc2bb01942d5b28d426be9176993
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05612381

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