Sodium Hydroxide → 3-amino-N-[2-bromo-6-chloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-4-cyanobenzamide

HRID 1970841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970841
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:20])([C:16]([F:19])([F:18])[F:17])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[C:4]([Cl:21])[C:3]=1[NH:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([N+:32]([O-])=O)[CH:25]=1.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[NH2:32][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[C:30]#[N:31])[C:23]([NH:22][C:3]1[C:4]([Cl:21])=[CH:5][C:6]([C:8]([F:20])([C:16]([F:17])([F:18])[F:19])[C:9]([F:14])([F:15])[C:10]([F:11])([F:12])[F:13])=[CH:7][C:2]=1[Br:1])=[O:35]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 86665275N-[2-bromo-6-chloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-4-cyano-3-nitrobenzamide

Produkt 1

HCID 866652793-amino-N-[2-bromo-6-chloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-4-cyanobenzamideAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-[2-bromo-6-chloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethyl-propyl)phenyl]-4-cyano-3-nitrobenzamide (Example 1.1) (92.7 g, 154.8 mmol) in tetrahydrofuran (800 ml) was added aqueous sodium hydroxide (0.1 M) (270 ml), sodium hydrosulfite (80.9 g, 464.4 mmol) and tetrabutylammonium bromide (“TBAB”) (4.99 g, 15.5 mmol). The reaction mixture was stirred at ambient temperature for 90 minutes. The phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with water, aqueous sodium hydrogen carbonate (10% w/v) (400 ml) and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent:cyclohexane/ethyl acetate 5:1) to give 3-amino-N-[2-bromo-6-chloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-4-cyanobenzamide (69 g, 78.4% yield). 1H NMR (400 MHz, CDCl3): 7.82 (s, 1H), 7.75 (s, 1H), 7.71 (s, 1H), 7.51 (m, 1H), 7.35 (s, 1H), 7.21 (m, 1H), 4.7 (s, 2H).

Aufarbeitung

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with water, aqueous sodium hydrogen carbonate (10% w/v) (400 ml) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent:cyclohexane/ethyl acetate 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-c16818541bc244f5a1cb4fcb41dc4ba4
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431514B2

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