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

HRID 362996Notes

Reaction equation

HRID 362996 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-883cb88fbc2c44288b47299c0421a74e
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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