Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Ethyl (5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetate

HRID 1372683

Reaktionsgleichung

Reaktionsgleichung von HRID 1372683
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:15]([F:26])[CH:14]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[Cl:19][C:18]1[C:13]([NH:12][C:2]2[S:3][C:4]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:5]=3[N:6]=2)=[CH:14][C:15]([F:26])=[C:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=1

Komponenten

5

Edukt 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 17858807Ethyl 4-amino-5-chloro-2-fluorophenylacetateHCID 178593962-Bromo-5-fluorobenzo[d]thiazole

Produkt 1

HCID 58778765Ethyl (5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

In xylene (5 ml), 2-bromo-5-fluorobenzothiazole (548 mg, 2.36 mmol), ethyl 4-amino-5-chloro-2-fluorophenylacetate (547 mg, 2.36 mmol), and pyridinium p-toluenesulfonate (PPTS) (178 mg, 0.71 mmol) were heated under reflux for 3 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1, v/v) eluate fractions, ethyl (5-chloro-4-(5-fluoro-2-benzothiazolyl)amino-2-fluorophenyl)acetate (298 mg, 33%) was obtained as a pale yellow solid.

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1

Quellen und Nachweise

ORD-Eintrag
ord-85eddbaed34b4d8eb09ca2a0baae7bdd
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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