Reaktion #63493

Reaktionsgleichung

sodium ethylate

tert-butyl hypochlorite

3-(2,3-dihydro-6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea

dimethyl sulfide

triethylamine

→

3-(6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea

Ausbeute 25.9%

Lösungsmittel

ethanol

water

methylene chloride

methylene choride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwithin 10 minutes
2. 2
   Extraktionextracted with methylene chloride
3. 3
   Sonstigethe organic phase is dried
4. 4
   Sonstigeevaporated

Vorschrift

A solution of 0.4 mmol of tert-butyl hypochlorite in 2 ml of methylene chloride is added dropwise to a solution of 0.3 mmol of 3-(2,3-dihydro-6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea, 0.4 mmol of dimethyl sulfide, and 0.3 mmol of triethylamine in 5 ml of methylene choride at -70° C., and the mixture is agitated for 2 hours. Then a solution of 2 mmol of sodium ethylate in 2 ml of ethanol is added thereto within 10 minutes, and the mixture is warmed up to room temperature within 2 hours, whereafter it is combined with water, extracted with methylene chloride, the organic phase is dried and evaporated. Chromatography on silica gel with methylene chloride/methanol (5%) yields 30 mg of 3-(6-methyl-13-nitro-8β-ergolinyl)-1,1-diethylurea.

Quelle