Réaction #836422

Équation de réaction

7-acetyl-4-hydroxy-1,3-benzothiazol-2(3H)-one

DMF

N,N-diisopropylethylamine

benzyl bromide

→

title compound

7-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

Solvants

Water

THF

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture extracted with ethyl acetate
2. 2
   Lavagewashed with brine
3. 3
   Séchagedried (MgSO4)
4. 4
   Autreevaporated in vacuo
5. 5
   AutreThe residue was purified on a 5 g silica SPE cartridge
6. 6
   Lavageeluting with a stepped gradient of 10% to 50% ethyl acetate-cyclohexane mixtures

Mode opératoire

To a solution of 7-acetyl-4-hydroxy-1,3-benzothiazol-2(3H)-one (153 mg), in dry THF (3 ml) and dry DMF (0.5 ml) under nitrogen, was added N,N-diisopropylethylamine (0.13 ml) and benzyl bromide (0.09 ml), and the mixture stirred for 72 h. Water (10 ml) was added and the mixture extracted with ethyl acetate. The organic phases were combined, washed with brine, dried (MgSO4), and evaporated in vacuo. The residue was purified on a 5 g silica SPE cartridge, eluting with a stepped gradient of 10% to 50% ethyl acetate-cyclohexane mixtures, to give the title compound (68 mg). LCMS RT=3.14 min.

Source