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Hydrochloric Acid → 5-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 888460
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 888460
[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([N+:30]([O-])=O)[CH:29]=1)[C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]([F:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[CH:11][C:10]=1[CH3:26])=[O:7])#[N:2].[Sn](Cl)(Cl)(Cl)Cl.Cl>C(O)(C)C>[NH2:30][C:28]1[CH:29]=[C:3]([C:1]#[N:2])[CH:4]=[C:5]([CH:27]=1)[C:6]([NH:8][C:9]1[C:10]([CH3:26])=[CH:11][C:12]([C:16]([F:25])([C:17]([F:18])([F:19])[F:20])[C:21]([F:22])([F:23])[F:24])=[CH:13][C:14]=1[CH3:15])=[O:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 592269403-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-5-nitro-benzamide

Produkt 1

HCID 592269545-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamideAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776
Isopropanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-5-nitro-benzamide (12.0 g, 25.9 mmol) (Example I5) was dissolved in isopropanol (200 ml) and tin chloride (14.73 g, 77.7 mmol) was added. The mixture was cooled to 0° C. and aqueous hydrochloric acid (concentrated) (30 ml) was added slowly. The reaction mixture was stirred at 80° C. for 0.5 hours. ⅓ of the total volume of isopropanol was evaporated. Water (100 ml) was added to the concentrated mixture and aqueous sodium hydroxide (4N) was added to adjust the pH to 7-8. The aqueous phase was extracted three times with ethyl acetate (3×200 ml). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1 to 0:1) to give 5-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (10.6 g, 94.4% yield). 1H-NMR (400 MHz, CDCl3): 7.47 (s, 1H), 7.44 (s, 2H), 7.36 (s, 2H), 7.07 (s, 1H), 4.11 (bs, 2H), 2.32 (s, 6H) ppm.

Aufarbeitung

  1. custom⅓ of the total volume of isopropanol was evaporated
  2. additionWater (100 ml) was added to the concentrated mixture and aqueous sodium hydroxide (4N)
  3. additionwas added
  4. extractionThe aqueous phase was extracted three times with ethyl acetate (3×200 ml)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1 to 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-fc74e3fd21b34c1dbe1c14c0fe15647c
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247594B2

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