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Ammonia → 1,1-Diethyl-3-(2,6,13-trimethyl-8alpha-ergolinyl)-urea

HRID 35854
ノート
印刷プレビュー

反応式

HRID 35854 の反応式
[CH2:1]([N:3]([CH2:27][CH3:28])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][C:17]([CH2:23]O)=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:25])[N:9]([CH3:26])[CH2:8]1)=[O:5])[CH3:2].CC(C)(C)C(Cl)=O.N.[Li].[Cl-].[NH4+]>N1C=CC=CC=1.C(Cl)(Cl)Cl.O>[CH2:27]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][C:17]([CH3:23])=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:25])[N:9]([CH3:26])[CH2:8]1)=[O:5])[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 3028194LithiumHCID 677875701,1-Diethyl-3-(2,6-dimethyl-13-hydroxymethyl-8alpha-ergolinyl)-urea

生成物 1

HCID 677880861,1-Diethyl-3-(2,6,13-trimethyl-8alpha-ergolinyl)-urea

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

実験手順

715 mg of 1,1-diethyl-3-(2,6-dimethyl-13-hydroxymethyl- 8alpha-ergolinyl)-urea (1.5 mmol) is dissolved in 10 ml of pyridine and mixed with 2 ml of trimethylacetyl chloride. Ice is added after 30 minutes of stirring at room temperature, it is stirred for another 30 minutes, made alkaline with ammonia and the mixture is cooled in an ice bath. The precipitated crystals are suctioned off, yield 785 mg, [α]D =-2° (0.5% in chloroform). The mother liquor is extracted with dichloromethane, dried and concentrated by evaporation. Both fractions are dissolved together in 6 ml of tetrahydrofuran and the solution is instilled in 50 ml of condensed, anhydrous ammonia. Then, it is mixed with 160 mg of lithium and the blue solution is stirred for 30 minutes at -40° C. Solid ammonium chloride, until decolorization, and 5 ml water are added in succession, the ammonia is evaporated and it is diluted with 80 ml of water. After 30 minutes of stirring in an ice bath, the precipitated crystals are suctioned off and dried in a vacuum, yield 643 mg (94% of theory), [α]D =+3° (0.5% in chloroform).

後処理

  1. additionIce is added after 30 minutes
  2. stirringit is stirred for another 30 minutes
  3. temperaturethe mixture is cooled in an ice bath
  4. extractionThe mother liquor is extracted with dichloromethane
  5. customdried
  6. concentrationconcentrated by evaporation
  7. dissolutionBoth fractions are dissolved together in 6 ml of tetrahydrofuran
  8. customthe solution is instilled in 50 ml of condensed, anhydrous ammonia
  9. stirringthe blue solution is stirred for 30 minutes at -40° C
  10. customthe ammonia is evaporated
  11. additionit is diluted with 80 ml of water
  12. stirringAfter 30 minutes of stirring in an ice bath
  13. dry with materialdried in a vacuum, yield 643 mg (94% of theory), [α]D =+3° (0.5% in chloroform)

出典と根拠

ORDレコード
ord-c1b7db1dda884d918fbc311a9a3306bf
出典データセット
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05411966

反応ノート

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