Triethylamine → 3-(2-Cyano-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

HRID 231700

Reaktionsgleichung

Reaktionsgleichung von HRID 231700
[CH3:1][CH2:2][N:3]([C:6]([NH:8][C@@H:9]1[CH2:24][N:23]([CH3:25])[C@H:22]2[C@@H:11]([C:12]3[C:17]4[C:18]([CH2:21]2)=[CH:19][NH:20][C:16]=4[CH:15]=[CH:14][CH:13]=3)[CH2:10]1)=[O:7])[CH2:4][CH3:5].[CH2:26]([N:28](CC)CC)C.ClS(N=C=O)(=O)=O>C(#N)C>[C:26]([C:19]1[NH:20][C:16]2[C:17]3[C:18]=1[CH2:21][C@@H:22]1[C@@H:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]([NH:8][C:6](=[O:7])[N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[CH2:24][N:23]1[CH3:25])#[N:28]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 443951Terguride

Produkt 1

HCID 135590143-(2-Cyano-6-methyl-8alpha-ergolinyl)-1,1-diethylureaAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

680 mg of terguride (2 mmol) is dissolved in 120 ml of acetonitrile and 5.5 ml of triethylamine and, under ice cooling, a solution of 3.5 ml of chlorosulfonyl isocyanate in 40 ml of acetonitrile is added dropwise thereto under an argon atmosphere. The ice bath is removed and the mixture allowed to stand for two days at room temperature. To facilitate isolation of the polar by-products, the mixture is combined with 20 ml of diethylamine and stirred for three hours at room temperature. Then the mixture is diluted with methylene chloride, extracted with 1N sodium hydroxide solution, and the water phase is once more extracted. The combined organic phases are dried with sodium sulfate and evaporated. The residue is chromatographed on silica gel with a mixture of methylene chloride and methanol, thus isolating 229 mg (31% of theory) of crude 3-(2-cyano-6-methyl-8α-ergolinyl)-1,1-diethylurea. After crystallizing from ethyl acetate, 92 mg is obtained as the pure compound.

Aufarbeitung

  1. customThe ice bath is removed
  2. additionThen the mixture is diluted with methylene chloride
  3. extractionextracted with 1N sodium hydroxide solution
  4. extractionthe water phase is once more extracted
  5. dry with materialThe combined organic phases are dried with sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with a mixture of methylene chloride and methanol

Quellen und Nachweise

ORD-Eintrag
ord-b3d790d3590944d1b14d3a9dadecb3ae
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847262

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