2-Amino-2',5-dichlorobenzophenone → HCID 15586650, compound

HRID 543604Notes

Reaction equation

HRID 543604 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:9][C:10]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])=[O:13].CO.C1C=CC=CC=1>C(Cl)Cl>[NH2:1][C:2]1[C:3]([NH:9][C:10]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[O:13])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180692-Amino-2',5-dichlorobenzophenoneHCID 805282-Chloro-3-pyridylamineHCID 21927730Benzene methanol

Product 1

HCID 15586650HCID 15586650, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
190 °C

Procedure

A stirred mixture of 20.0 g (0.156 mole) of 3-amino-2-chloropyridine and 37.3 g (0.14 mole) of 2-amino-2',5-dichlorobenzophenone was heated at 190° C. under nitrogen atmosphere for 5.5 hr. Thin layer chromatography (5% methyl alcohol-benzene on silica gel) indicated reaction had not substantially occurred. The mixture was stirred overnight at 190° C., cooled somewhat, and 100 ml methylene chloride was added cautiously. The suspension was stirred for two hr and the black solid which formed was separated by filtration. The solid was suspended in 500 ml of methylene chloride and 300 ml of dilute sodium hydroxide was added. An emulsion formed and the mixture was filtered which allowed separation of layers. The methylene chloride layer was washed with two 250 ml portions of water by extraction, dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in benzene and filtered through a 300 g column of florisil to remove low Rf material. All fractions were combined and evaporated under reduced pressure. Thin layer chromatography showed presence of two major components with lower Rf spot predominating. The residue was dissolved in benzene and chromatographed on a 600 g column of florisil packed in benzene. The higher Rf material was eluted with 1% acetone-benzene. On evaporation, the residue was triturated in benzene and recrystallized from benzene-isooctane to give 2.7 g product; m.p. 162°-4° C.

Workup

  1. customreaction
  2. temperaturecooled somewhat
  3. stirringThe suspension was stirred for two hr
  4. customthe black solid which formed
  5. customwas separated by filtration
  6. addition300 ml of dilute sodium hydroxide was added
  7. customAn emulsion formed
  8. filtrationthe mixture was filtered which
  9. customseparation of layers
  10. washThe methylene chloride layer was washed with two 250 ml portions of water by extraction
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. dissolutionThe residue was dissolved in benzene
  14. filtrationfiltered through a 300 g column of florisil
  15. customto remove low Rf material
  16. customevaporated under reduced pressure
  17. dissolutionThe residue was dissolved in benzene
  18. customchromatographed on a 600 g column of florisil
  19. washThe higher Rf material was eluted with 1% acetone-benzene
  20. customOn evaporation
  21. customthe residue was triturated in benzene
  22. customrecrystallized from benzene-isooctane

Sources & evidence

ORD record
ord-dce6b91ffd074ac3b4b8ad635f4bd9f4
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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