HCID 178470049, Verbindung → Ethyl 2-(5-bromobenzo[D]thiazol-2-YL)acetate

HRID 424941

Reaktionsgleichung

Reaktionsgleichung von HRID 424941
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=2[NH:10][C:11]=1O)=[O:5])[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:11]1[S:7][C:8]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=2[N:10]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 178470049HCID 178470049, Verbindung

Produkt 1

HCID 21041508Ethyl 2-(5-bromobenzo[D]thiazol-2-YL)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of the crude material from Example 2C (2.7 g, 8.5 mmol) in acetic acid (60 mL) and heated to 110° C. Then Zn (18 equivalents) was added slowly in portions over 30 min to the mixture under nitrogen. After the completion the mixture was cooled to room temperature and the Zn residue was filtered off. The filter cake was washed with MeOH. And the combined filtrate was stripped to dryness. The residue was dissolved in 70 mL of chloroform and washed with water twice. The chloroform solution was dried with anhydrous MgSO4 and concentrated to dryness. The crude product was purified by column chromatography (silica gel, 10% EtOAc/Hexane). Purified yield for the three steps from example 2B-2D was 1.11 g (43.3%).

Aufarbeitung

  1. temperatureAfter the completion the mixture was cooled to room temperature
  2. filtrationthe Zn residue was filtered off
  3. washThe filter cake was washed with MeOH
  4. dissolutionThe residue was dissolved in 70 mL of chloroform
  5. washwashed with water twice
  6. dry with materialThe chloroform solution was dried with anhydrous MgSO4
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified by column chromatography (silica gel, 10% EtOAc/Hexane)
  9. customPurified
  10. customyield for the three steps from example 2B-2D

Quellen und Nachweise

ORD-Eintrag
ord-0c77c925ecbb4075b1c0c6b60347fb41
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106088B2

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