Phenyltrimethylammonium bromide dibromide → 4-(Benzyloxy)-7-(bromoacetyl)-1,3-benzothiazol-2(3H)-one

HRID 749241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749241
[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br-:22].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1.O>[CH2:15]([O:14][C:7]1[C:8]2[NH:9][C:10](=[O:13])[S:11][C:12]=2[C:4]([C:1](=[O:3])[CH2:2][Br:22])=[CH:5][CH:6]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 693219837-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

Produkt 1

HCID 859396374-(Benzyloxy)-7-(bromoacetyl)-1,3-benzothiazol-2(3H)-oneAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 7-acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one (68 mg) in dry THF (3 ml) under nitrogen, was added phenyltrimethylammonium tribromide (90 mg) and the mixture heated at 80° C. under nitrogen for 2 h. The mixture was diluted with water, extracted with ethyl acetate, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a 5 g silica SPE cartridge, eluting with stepped gradient of 10% to 100% ethyl acetate-cyclohexane mixtures, to give the title compound (49 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a 5 g silica SPE cartridge
  6. washeluting

Quellen und Nachweise

ORD-Eintrag
ord-400103016d584ac1b294435029fd05bf
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402598B2

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