Hydrochloric Acid → HCID 20437461, compound

HRID 1980114Notes

Reaction equation

HRID 1980114 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[CH:7][CH:8]=1.C([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].C1C2C(CCCC2)CCC1.Cl>C(O)C.[Cu].CC(C)=O>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7044DecalinHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 11430Potassium CarbonateHCID 75937N-(p-acetylphenyl)acetamide

Product 1

HCID 20437461HCID 20437461, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 13.0 g of m-trifluoromethylphenyl bromide, 8.68 g of p-acetylaminoacetophenone, 14.5 g of potassium carbonate, 0.45 g of copper powder and 40 ml of decahydronaphthalene was stirred at reflux on an oil bath at 200° C., under argon for 64 hours. The mixture was then cooled, stirred with 200 ml of acetone, filtered and the filtrate evaporated to a semi-solid. Evaporative distillation gave a semi-solid which was dissolved in 150 ml of ethanol and 150 ml of concentrated hydrochloric acid and refluxed under argon for 30 minutes. The mixture was cooled, partially evaporated and partitioned between 50% saturated brine and ethyl acetate. The ethyl acetate layer was washed with water and brine, dried and evaporated to a semi-solid. This semi-solid was purified by chromatography, giving 4'-[3-(trifluoromethyl)phenylamino]acetophenone which was then converted to the desired product by the procedure of Example 9, giving the product as a light amber solid, m.p. 180°-195° C. (dec.).

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated to a semi-solid
  4. distillationEvaporative distillation
  5. customgave a semi-solid which
  6. temperatureThe mixture was cooled
  7. custompartially evaporated
  8. custompartitioned between 50% saturated brine and ethyl acetate
  9. washThe ethyl acetate layer was washed with water and brine
  10. customdried
  11. customevaporated to a semi-solid
  12. customThis semi-solid was purified by chromatography

Sources & evidence

ORD record
ord-02a1cafca74148bd8ce2963ac6f7d7b6
Source dataset
uspto-grants-1984_11
Patent number
US04485114

Reaction notes

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