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

HRID 1943093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943093
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH2:19].N1C=CC=CC=1.S(=[N:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[Br:38])[C:32](Cl)=[O:33])=O>O1CCCC1>[NH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[Br:38])[C:32]([NH:19][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([C:8]([F:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:5][C:4]=1[CH3:18])=[O:33]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 98824254-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2,6-dimethylanilineHCID 594448243-Sulfinylamino-4-bromo-benzoyl chloride

Produkt 1

HCID 594448253-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (0.31 g, 1.1 mmol) (prepared according to EP 1,006,102) in anhydrous tetrahydrofuran (2 ml), at 20° C., was added sequentially pyridine (0.174 g, 2.2 mmol) and a solution of 3-sulfinylamino-benzoyl chloride (0.25 g, 0.86 mmol) (Example 1.2) in anhydrous tetrahydrofuran (2 ml). The reaction mixture was stirred at ambient temperature for three hours. The reaction mixture was quenched by addition of water (5 ml). After separation of the phases, the aqueous layer was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:3) to give 3-amino-4-bromo-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.235 g, 78% yield). 1H-NMR (DMSO-d6, 400 MHz): 7.53 (d, 1H), 7.44 (s, 2H), 7.38 (d, 1H), 7.10 (q, 1H), 5.6 (s, 2H), 2.24 (s, 6H) ppm.

Aufarbeitung

  1. customThe reaction mixture was quenched by addition of water (5 ml)
  2. customAfter separation of the phases
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-87502b173ede479a8a111a2f4fff3c6f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389767B2

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