2-(2-Chloro-ethoxy)-6-nitro-phenylamine → 2-(2-Chloro-ethoxy)-4-chloro-6-nitro-phenylamine

HRID 365399Notes

Reaction equation

HRID 365399 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14].[Cl:15]NC(=O)CCC(N)=O>C(#N)C>[Cl:15][C:9]1[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]([NH2:14])=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[CH:10]=1

Participants

4

Reactant 2

HCID 111719662-(2-Chloro-ethoxy)-6-nitro-phenylamineHCID 15238416N-chlorosuccinamide

Product 1

HCID 113571672-(2-Chloro-ethoxy)-4-chloro-6-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2-chloro-ethoxy)-6-nitro-phenylamine (2a, 30.0 g, 0.14 mol), N-chlorosuccinamide and acetonitrile (1.3 L) was refluxed for 4 hr. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (500 mL). The organic layer was washed with water (2X, 250 mL) and brine (250 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to give an orange solid residue. Crystallization from ethyl acetate-hexane gave 33.5 g (95.3%) as orange solid, mp 109-110° C.; MS EI m/e 250/252/254 (M+).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue was diluted with ethyl acetate (500 mL)
  3. washThe organic layer was washed with water (2X, 250 mL) and brine (250 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customto give an orange solid residue
  8. customCrystallization from ethyl acetate-hexane
  9. customgave 33.5 g (95.3%) as orange solid, mp 109-110° C.

Sources & evidence

ORD record
ord-013e502d9448446ab8dc21de0b70d835
Source dataset
uspto-grants-2000_10
Patent number
US06127380

Reaction notes

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