3-Nitroaniline → 2-(2-Methoxy-ethoxy)-N-(3-nitro-phenyl)-acetamide

HRID 1787707Notes

Reaction equation

HRID 1787707 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=O.ClC(OCC(C)C)=O.[N+:18]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])([O-:20])=[O:19].C(=O)(O)[O-].[Na+]>O1CCCC1.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([NH:24][C:23]1[CH:25]=[CH:26][CH:27]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=1)=[O:9]

Participants

7

Reactant 4

HCID 74233-NitroanilineHCID 27642(2-Methoxyethoxy)acetic acidHCID 62365Isobutyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 430376262-(2-Methoxy-ethoxy)-N-(3-nitro-phenyl)-acetamideYield 81.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

5 g of (2-methoxyethoxy)-acetic acid is dissolved in 500 ml of tetrahydrofuran. 9.7 ml of triethylamine and 5.6 ml of isobutyl chloroformate are added at 0° C., and it is stirred for 30 minutes at 0° C. 5.0 g of 3-nitroaniline is added, and it is stirred for another 15 hours at room temperature. The reaction mixture is mixed with semi-saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic solution is washed with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation and, after purification by chromatography on silica gel, 7.5 g of the title compound is obtained.

Workup

  1. stirringit is stirred for another 15 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic solution is washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customafter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-9f379d549df843f0bbefe14fa3bf253a
Source dataset
uspto-grants-2009_03
Patent number
US07511059B2

Reaction notes

Loading…