Hydrochloric Acid → 2-Chloro-5-[(2,2,2-trifluoroethylamino)sulfonyl]-4-fluorobenzoic acid

HRID 1992135

Reaktionsgleichung

Reaktionsgleichung von HRID 1992135
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].C([O-])(O)=O.[Na+].[F:20][C:21]([F:25])([F:24])[CH2:22][NH2:23].[ClH:26]>O>[Cl:26][C:11]1[CH:12]=[C:13]([F:14])[C:5]([S:2]([NH:23][CH2:22][C:21]([F:25])([F:24])[F:20])(=[O:4])=[O:3])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 516892Sodium BicarbonateHCID 39298913-(Chlorosulfonyl)-4-fluorobenzoic acid

Produkt 1

HCID 587285292-Chloro-5-[(2,2,2-trifluoroethylamino)sulfonyl]-4-fluorobenzoic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4.997 g (18.3 mmol) 3-chlorosulfonyl-4-fluorobenzoic acid, 2.90 g (27.5 mmol) NaHCO3 were dissolved in 50 mL water. 1.45 mL (18.3 mmol) trifluoroethylamine was added dropwise to solution. Solution was acidified to pH=1 with concentrated HCl and product was extracted into ethyl acetate. Dried over MgSO4 and concentrated. 5.27 g recovered (83% yield). Crude product was used in subsequent step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 9.22-9.37 (dt, 1H, J=6.44, 30.24 Hz), 7.80-7.92 (dd, 1H, J=9.91, 25.78 Hz), 4.04-4.16 (m, 1H), 3.77-3.90 (m, 1H).

Aufarbeitung

  1. extractionwas extracted into ethyl acetate
  2. dry with materialDried over MgSO4
  3. concentrationconcentrated
  4. custom5.27 g recovered (83% yield)
  5. customCrude product was used in subsequent step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-795f4929ed5d4ea8ada4c0f47ece15e8
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645771B2

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