Bromine → 2-Methyl-6-phenoxy-benzothiazole

HRID 415692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415692
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[S:17])[CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr>C(Cl)Cl>[CH3:16][C:15]1[S:17][C:10]2[CH:9]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:13]=[CH:12][C:11]=2[N:14]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 59402779N-(4-Phenoxy-phenyl)-thioacetamide

Produkt 1

HCID 38382522-Methyl-6-phenoxy-benzothiazoleAusbeute 10,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To an ice-cold solution of N-(4-phenoxy-phenyl)-thioacetamide (0.78 g, 3.20 mmol) in 10 ml of DCM was added Br2 (0.32 ml, 6.40 mmol) dropwise. The reaction mixture was heated at 45° C. for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated under reduced pressure. The residue was basified with NH4OH solution and extracted with ethyl acetate. The combined organics were, dried, (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica (230-400 M) using ethyl acetate/hexane (3:97) as the eluent to provide the title compound (0.08 g, 10.3%).

Aufarbeitung

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialdried, (Na2SO4),
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica (230-400 M)

Quellen und Nachweise

ORD-Eintrag
ord-793f121e1d1c4e65a018fc45a5c1b80b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088791B2

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