Methyl 2-(4-amino-3-chlorophenyl)acetate → Methyl (3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl)acetate

HRID 1372681

Reaktionsgleichung

Reaktionsgleichung von HRID 1372681
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[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[Cl:24].[NH+]1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:5]=2[N:6]=1

Komponenten

5

Edukt 3

HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetateHCID 178593962-Bromo-5-fluorobenzo[d]thiazoleHCID 22033616Pyridinium.p-toluenesulfonate

Produkt 1

HCID 58778358Methyl (3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl)acetateAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

In xylene (5 ml), 2-bromo-5-fluorobenzothiazole (516 mg, 2.22 mmol), methyl 4-amino-3-chlorophenylacetate (444 mg, 2.22 mmol), and pyridinium•p-toluenesulfonate (PPTS) (168 mg, 0.67 mmol) were heated under reflux for 10 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, methyl (3-chloro-4-(5-fluoro-2-benzothiazolyl)aminophenyl)acetate (292 mg, 37%) was obtained as a pale yellow oil.

Aufarbeitung

  1. temperatureunder reflux for 10 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-4c7368b2558a4b6f8b6eb27100b196f9
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

Verknüpfte Notizen

Wird geladen…