Pyridine → 3-amino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943092Notes

Reaction equation

HRID 1943092 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH2:20])[CH3:2].N1C=CC=CC=1.S(=[N:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34])=O>ClCCl>[NH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([NH:20][C:4]1[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17])=[CH:8][C:3]=1[CH2:1][CH3:2])=[O:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12238911Benzoyl chloride, 3-(sulfinylamino)-HCID 227346102-Methyl-6-ethyl-4-(heptafluoro-prop-2-yl)-aniline

Product 1

HCID 441994443-amino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (2.09 g, 6.9 mmol) (prepared according to EP 1,006,102) in dichloromethane (30 ml) under stirring at 25° C., was added sequentially pyridine (0.8 ml, 9.9 mmol) and a solution of 3-sulfinylamino-benzoyl chloride (1.39 g, 6.9 mmol) (Example 1.1) in dichloromethane (7 ml). The reaction mixture was stirred at ambient temperature for 6 hours. The reaction mixture was quenched by addition of aqueous hydrochloric acid (2N) (4 ml) and stirred vigorously for 20 minutes. The mixture was diluted with water (20 ml) and the phases separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed successively with aqueous sodium hydrogen carbonate (saturated) and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4 to 3:2). After evaporation of the solvents, the yellow oil was triturated with hexane, where it crystallized. The desired compound was isolated as white crystals. M.p. 143-145° C. 1H-NMR as described for Example 3.1.

Workup

  1. customThe reaction mixture was quenched by addition of aqueous hydrochloric acid (2N) (4 ml)
  2. stirringstirred vigorously for 20 minutes
  3. additionThe mixture was diluted with water (20 ml)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. washThe combined organic phases were washed successively with aqueous sodium hydrogen carbonate (saturated) and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4 to 3:2)
  10. customAfter evaporation of the solvents
  11. customthe yellow oil was triturated with hexane, where it
  12. customcrystallized

Sources & evidence

ORD record
ord-331a5f0311504c8f95227458b62d9b2d
Source dataset
uspto-grants-2013_03
Patent number
US08389767B2

Reaction notes

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