Hydrochloric Acid → HCID 23108272, compound

HRID 494680Notes

Reaction equation

HRID 494680 reaction equation
FC(F)(F)C([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:8][C:7]=1[CH3:23])=O.Cl>O>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:9]2[CH:8]=[C:7]([CH3:23])[C:6]([NH2:5])=[C:11]([CH3:12])[CH:10]=2)=[CH:18][CH:17]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86602535HCID 86602535, compound

Product 1

HCID 23108272HCID 23108272, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 ml round bottom flask was charged with 5.06 mmol (1.768 g) of 2,2,2-trifluoro-N-(4′-tert-butyl-3,5-dimethyl-biphenyl-4-yl)-acetamide, water (10 ml), and concentrated hydrochloric acid (10 ml). The mixture was heated to reflux for 17 h. The solution was allowed to cool to ambient temperature before it was evaporated to dryness. The residue was refluxed with Ba(OH)2.8H2O (9 g) in 100 ml of water for 1.5 h and then cooled to room temperature. This aqueous solution was extracted three times with 20 ml of CHCl3. The organic layer was dried over MgSO4, filtered, evaporated and dried under vacuum. The resulting brown precipitate of 4′-tert-butyl-3,5-dimethyl-biphenyl-4-ylamine was obtained in 69% yield. 1H NMR (CDCl3): δ=1.37 (s, 9H, C(CH3)3); 2.27 (s, 6H, ortho-CH3); 7.30-7.31 (d, 2H, CHar); 7.44-7.50 (m, 4H, CHar), 13C NMR (CDCl3): δ=18.3 (ortho-CH3); 31.4 (CH3); 34.6 (C(CH3)3); 125.8 (CHar); 126.8 (CHar); 127.2 (CHar); 135.5 (CHar); 137.3 (CHar); 141.4 (CHar); 150.7 (CHar).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 17 h
  3. customwas evaporated to dryness
  4. temperatureThe residue was refluxed with Ba(OH)2.8H2O (9 g) in 100 ml of water for 1.5 h
  5. temperaturecooled to room temperature
  6. extractionThis aqueous solution was extracted three times with 20 ml of CHCl3
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried under vacuum

Sources & evidence

ORD record
ord-12393dcf46b24d8c9f4c054858d62dae
Source dataset
uspto-grants-2009_05
Patent number
US07538172B2

Reaction notes

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