Ammonia → 1,1-Diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]urea

HRID 231709

反応式

HRID 231709 の反応式
C(O[CH2:4][CH3:5])=O.[CH:6]([SH:9])([SH:8])[CH3:7].[CH2:10]([N:12]([CH2:33][CH3:34])[C:13]([NH:15][C@H:16]1[CH2:30][C@H:29]2[C@@H:19]([CH2:20][C:21]3[C:31]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]2=4)[NH:23]C=3)[N:18]([CH3:32])[CH2:17]1)=[O:14])[CH3:11].N>C(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.O.CO>[CH2:33]([N:12]([CH2:10][CH3:11])[C:13]([NH:15][C@H:16]1[CH2:30][C@H:29]2[C@@H:19]([CH2:20][C:21]3[C:31]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]2=4)[NH:23][C:7]=3[CH:6]2[S:9][CH2:5][CH2:4][S:8]2)[N:18]([CH3:32])[CH2:17]1)=[O:14])[CH3:34]

参加物

9

反応物 4

HCID 222AmmoniaHCID 8025Ethyl formateHCID 336451,1-EthanedithiolHCID 443951Terguride

生成物 1

HCID 867420541,1-Diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]urea収率 42%

試薬・触媒・溶媒 4

HCID 24193Titanium Tetrachloride触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒2 回

実験手順

At room temperature under argon, 7 ml of ethyl formate and 3.6 ml (44 mmol) of ethanedithiol are added in succession to a solution of 6.8 g of 1,1-diethyl-3-(6-methyl-8α-ergolinyl)urea in 200 ml of chloroform. Thereafter 8.8 ml (80 mmol) of titanium(IV) chloride dissolved in 100 ml of chloroform is added gradually dropwise to the mixture. The latter is stirred for 20 hours at room temperature. Although the starting material is not as yet entirely converted at this point in time, the reaction mixture is worked up to avoid further formation of the disubstituted compound. For this purpose, the reaction mixture is cooled in an ice bath and combined, in sequence, dropwise with 50 ml of methanol and 40 ml of water. The mixture is then made alkaline with 25% ammonia solution and extracted with methylene chloride. The organic phases are washed with water and dried over magnesium sulfate. The evaporated residue is crystallized in boiling heat from methanol/ethyl acetate, thus obtaining 3.8 g of 1,1-diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8α-ergolinyl]urea (42% yield).

後処理

  1. additionis added gradually dropwise to the mixture
  2. temperatureFor this purpose, the reaction mixture is cooled in an ice bath
  3. extractionextracted with methylene chloride
  4. washThe organic phases are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe evaporated residue is crystallized
  7. temperaturein boiling heat from methanol/ethyl acetate

出典と根拠

ORDレコード
ord-f5f5ba45034d40d79cd3c367248f3e5e
出典データセット
uspto-grants-1989_07
特許番号
US04847262

関連ノート

読み込み中…