3-Nitroaniline → 2-chloro-N-(3-nitrophenyl)acetamide

HRID 1787710Notes

Reaction equation

HRID 1787710 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.ClC(O[C:22]([Cl:24])=O)=O.[C:25](=O)(O)[O-:26].[Na+]>O1CCCC1>[Cl:24][CH2:22][C:25]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:26]

Participants

6

Reactant 4

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 15856549Chloroformic acid anhydride

Product 1

HCID 5320662-chloro-N-(3-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.8 g of 3-nitroaniline is dissolved in 500 ml of tetrahydrofuran. 30.5 ml of triethylamine and 19.4 g of chloroformic acid anhydride are added at 0° C. It is stirred for 12 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, 20.0 g of the title compound is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution is washed with saturated sodium chloride solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customafter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-89573fb1735a40b7a8f339fe3cdb01ad
Source dataset
uspto-grants-2009_03
Patent number
US07511059B2

Reaction notes

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