2-Bromo-6-chlorobenzo[d]thiazole → Methyl (4-(6-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetate

HRID 1372676

Reaktionsgleichung

Reaktionsgleichung von HRID 1372676
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[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:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=3[Cl:24])[S:3][C:4]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 114997622-Bromo-6-chlorobenzo[d]thiazoleHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetateHCID 22033616Pyridinium.p-toluenesulfonate

Produkt 1

HCID 58778710Methyl (4-(6-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetateAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

In xylene (10 ml), 2-bromo-6-chlorobenzothiazole (760 mg, 3.06 mmol), methyl 4-amino-3-chlorophenylacetate (610 mg, 3.06 mmol), and pyridinium•p-toluenesulfonate (PPTS) (230 mg, 0.92 mmol) were heated under reflux for 1 hour. 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 (6:1, v/v) eluate fractions, methyl (4-(6-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetate (271 mg, 24%) was obtained as a pale yellow solid.

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  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 (6:1

Quellen und Nachweise

ORD-Eintrag
ord-132831e55ece48d098a49cee79ce59c0
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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