Sodium hydride → HCID 13365280、化合物

HRID 615318ノート

反応式

HRID 615318 の反応式
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13](=[O:14])[NH:12][C:11]([S:15][CH3:16])=[C:10]2[C:17]#[N:18])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][CH2:32]Cl>O1CCOCC1>[CH3:25][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13](=[O:14])[N:12]([CH2:32][CH2:31][CH2:30][N:29]([CH3:34])[CH3:28])[C:11]([S:15][CH3:16])=[C:10]2[C:17]#[N:18])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 132362024-[4-(Dimethylamino)phenyl]-2-(methylsulfanyl)-5-oxo-4-(pyridin-3-yl)-4,5-dihydro-1H-pyrrole-3-carbonitrile

生成物 1

HCID 13365280HCID 13365280、化合物収率 41.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 3.5 g 4-(4-dimethylaminophenyl)-2-methylthio-5-oxo-4-(3-pyridyl)-2-pyrroline-3-carbonitrile and 0.3 g sodium hydride (80% in white oil) is refluxed for one hour. One then adds dropwise thereto, within ten minutes, a solution of 1.3 g 3-dimethylaminopropyl chloride in 25 ml abs. dioxan and further boils for six hours. After cooling, the reaction mixture is filtered, the solvent is removed on a Rotavapor and the residue is chromatographed on silica gel with chloroform+methanol 10+1 as elution agent. After crystallization of the main fraction from isopropanol, one obtains 1.8 g of colorless crystals of mp 90°-91° C.

後処理

  1. temperatureis refluxed for one hour
  2. additionOne then adds dropwise
  3. waitwithin ten minutes
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture is filtered
  6. customthe solvent is removed on a Rotavapor
  7. customthe residue is chromatographed on silica gel with chloroform+methanol 10+1 as elution agent
  8. customAfter crystallization of the main fraction from isopropanol, one

出典と根拠

ORDレコード
ord-0b9af09f6446479f877c6223c5568365
出典データセット
uspto-grants-1985_02
特許番号
US04499089

反応ノート

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