Reaktion #318879

ord-785548c2b37c4317b711fc0f57b58362

Reaktionsgleichung

CCN(CC)C(=O)N[C@H]1C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
terguride
O=C1CCC(=O)N1I
N-iodosuccinimide
O=C([O-])O
bicarbonate
→
CCN(CC)C(=O)N[C@H]1C[C@@H]2c3cccc4[nH]c(I)c(c34)C[C@H]2N(C)C1
1,1-diethyl-3-(2-iodo-6-methyl-8α-ergolinyl)urea
Ausbeute 76.0%

Edukte

CCN(CC)C(=O)N[C@H]1C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
terguride
O=C1CCC(=O)N1I
N-iodosuccinimide
O=C([O-])O
bicarbonate

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with methylene chloride
  2. 2
    Trocknenthe organic phase is dried with magnesium sulfate
  3. 3
    SonstigeAfter evaporation of the solvent
  4. 4
    Sonstigethe residue is chromatographed on silica gel

Vorschrift

A solution is prepared from 1 mmol of terguride in 20 ml of anhydrous dioxane, combined with about 1.5 ml of N-iodosuccinimide at room temperature and stirred for 30 minutes. The reaction mixture is then poured into a saturated bicarbonate solution, extracted with methylene chloride and the organic phase is dried with magnesium sulfate. After evaporation of the solvent, the residue is chromatographed on silica gel, thus obtaining in a 76% yield 1,1-diethyl-3-(2-iodo-6-methyl-8α-ergolinyl)urea.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04847262uspto-grants-1989_07