Chlorosuccinimide → 4-(4-Chloronaphthoxy)-2,3,5-trichloroaniline

HRID 37325Notes

Reaction equation

HRID 37325 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:19]([Cl:20])=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[Cl:21])=[CH:4][CH:3]=1.[Cl:22]N1C(=O)CCC1=O>C1C=CC=CC=1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[C:14]([Cl:21])=[CH:15][C:16]([NH2:17])=[C:18]([Cl:22])[C:19]=2[Cl:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 138271123,5-Dichloro-4-[(4-chloronaphthalen-1-yl)oxy]aniline

Product 1

HCID 190725804-(4-Chloronaphthoxy)-2,3,5-trichloroanilineYield 56%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a magnetically stirred solution of 4-(4-chloro-1-naphthoxy)-3,5-dichloroaniline (6.00 grams, 17.72 mmol) prepared in Part B in benzene (50 milliliters) was added solid N-chlorosuccinimide (2.84 grams, 21.20 mmol). The mixture was heated to reflux for 1 hour, cooled and filtered. The solvent was evaporated under reduced pressure and the crude product when subjected to flash column chromatography (3:1 hexane:ethyl acetate) afforded pure 4-(4-chloronaphthoxy)-2,3,5-trichloroaniline (3.70 grams, 9.92 mmol, 56% ). Elemental analysis of the product indicated the following:

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a0c49f6912814278ac5d28312616860b
Source dataset
uspto-grants-1995_05
Patent number
US05420163

Reaction notes

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