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

HRID 1858364Notes

Reaction equation

HRID 1858364 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]N1C(=O)CCC1=O>C(#N)C>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([Cl:15])[CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 111719662-(2-Chloro-ethoxy)-6-nitro-phenylamine

Product 1

HCID 113571672-(2-Chloro-ethoxy)-4-chloro-6-nitro-phenylamineYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2-chloro-ethoxy)-6-nitro-phenylamine (30.0 g, 0.14 mol), N-chlorosuccinimide and acetonitrile (1.3 L) was refluxed for 4 hours. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (500 ml). The organic layer was washed with water (2×250 ml) and brine (250 ml), dried over anhydrous magnesium sulfate and filtered. The solvent was removed under vacuum to give an orange solid residue. Crystallization from ethyl acetate-hexanes gave 33.5 g (95.3%) of product as an orange solid: mp 109-110° C.; MS (EI) 250/252/254 m/e (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 (2×250 ml) and brine (250 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customto give an orange solid residue
  8. customCrystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-91b78bdf23c547e294fcda9cf1bcc0c4
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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