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Ammonia → 3-[9,10-Didehydro-2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]-1,1-diethylurea

HRID 231713
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 231713
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3]1.C(O[CH2:29][CH3:30])=O.[CH:31]([SH:34])([SH:33])C.N>C(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.O.CO>[S:33]1[CH2:30][CH2:29][S:34][CH:31]1[C:13]1[NH:12][C:11]2[C:17]3[C:14]=1[CH2:15][C@@H:16]1[C:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)=[CH:5][C@H:4]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3][N:2]1[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 222AmmoniaHCID 8025Ethyl formateHCID 28864LisurideHCID 336451,1-Ethanedithiol

Produkt 1

HCID 867420553-[9,10-Didehydro-2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]-1,1-diethylureaAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24193
Titanium Tetrachloride
Katalysator
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Under argon, 11.5 g (0.03 mol) of 3-(9,10-didehydro-6-methyl-8α-ergolinyl)-1,1-diethylurea is dissolved in 300 ml of chloroform. At room temperature, 105 ml of ethyl formate and 5.4 ml of ethanedithiol are added in succession. Then 13.2 ml of titanium(IV) chloride in 150 ml of chloroform is added dropwise. The mixture is agitated for 3 days at room temperature. To work up the mixture, it is cooled in an ice bath and 75 ml of methanol and 600 ml of water are added in sequence dropwise to this mixture. The solution is rendered alkaline with 60 ml of 25% ammonia solution and extracted with methylene chloride. The organic phases are washed with water and dried over magnesium sulfate. The concentrated residue is chromatographed under pressure on silica gel with ethyl acetate/methanol 95:5, thus isolating 1.7 g of 3-[9,10-didehydro-2-(1,3-dithiolan-2-yl)-6-methyl-8α-ergolinyl]-1,1-diethylurea (12% yield).

Aufarbeitung

  1. temperatureis cooled in an ice bath
  2. extractionextracted with methylene chloride
  3. washThe organic phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe concentrated residue is chromatographed under pressure on silica gel with ethyl acetate/methanol 95:5

Quellen und Nachweise

ORD-Eintrag
ord-0bd8e2a6c5414cce8d6f8ddc70fc0fb6
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04847262

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