Reaktion #1361816

Reaktionsgleichung

tert-Butyl(methylsulfonyl)carbamate

sodium hydride

3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

hydrochloric acid

→

title compound

Ausbeute 78.7%

{{5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}methyl}(methylsulfonyl)carbamic acid, tert-butyl ester

Ausbeute 78.7%

Lösungsmittel

tetrahydrofuran

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to room temperature
2. 2
   Extraktionextracted with methylene chloride
3. 3
   WaschenThe combined organic layers are washed with water
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe resultant residue is chromatographed on silica gel with ether

Vorschrift

tert-Butyl(methylsulfonyl)carbamate (1.52 g, 0.00780 mol) is added to a mixture of sodium hydride (60%, 0.312 g, 0.00780 mol) and tetrahydrofuran at 0° C. The mixture is allowed to come to room temperature. A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (3.00 g, 0.00714 mol) in dimethyl sulfoxide is added dropwise. The resultant mixture is stirred overnight at room temperature, poured into dilute hydrochloric acid, and extracted with methylene chloride. The combined organic layers are washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resultant residue is chromatographed on silica gel with ether:methylene chloride to give the title compound as a white solid (3.00 g, 78.7%, mp 109-111° C.) which is identified by NMR spectral analysis.

Quelle