Water → 2-(2-Azido-ethoxy)-4-chloro-6-nitro-phenylamine

HRID 1872846Notes

Reaction equation

HRID 1872846 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=1[NH2:15].[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C)C=O>[N:16]([CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=1[NH2:15])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 113571672-(2-Chloro-ethoxy)-4-chloro-6-nitro-phenylamine

Product 1

HCID 186876782-(2-Azido-ethoxy)-4-chloro-6-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(2-chloro-ethoxy)-4-chloro-6-nitro-phenylamine (3.07 g, 12.2 mmol), sodium azide (1.59 g, 24.4 mmol) in anhydrous N,N-dimethylformamide (30 ml) was allowed to heat at 60° C. for 18 hours. The reaction was poured into water (150 ml) and extracted with ethyl ether (2×100 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum to afford an orange solid. The solid was washed with ethyl ether (5 ml) to afford an orange crystalline solid: mp 113-114° C.

Workup

  1. extractionextracted with ethyl ether (2×100 ml)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum
  5. customto afford an orange solid
  6. washThe solid was washed with ethyl ether (5 ml)
  7. customto afford an orange crystalline solid

Sources & evidence

ORD record
ord-27a9b613100a43bd9c4cc7e005096298
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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