Phenyl Isothiocyanate → 2-Phenylthio-2-(3-phenyl-1,3-thiazolidine-2-yliden)acetonitrile

HRID 49957

反応式

HRID 49957 の反応式
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([S:16][CH2:17][C:18]#[N:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H-].[Na+].Br[CH2:23][CH2:24]Br>CN(C)C=O.CCOCC.O>[C:10]1([S:16][C:17](=[C:8]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:24][CH2:23][S:9]2)[C:18]#[N:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

8

反応物 4

HCID 7673Phenyl IsothiocyanateHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 78891(Phenylthio)acetonitrile

生成物 1

HCID 40797572-Phenylthio-2-(3-phenyl-1,3-thiazolidine-2-yliden)acetonitrile収率 60.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

18.9 g (140 mmols) of phenylisothiocyanate and 20.9 g (140 mmols) of phenylthioacetonitrile dissolved in 50 ml of dimethylformamlde were added dropwise with stirring at room temperature to a suspension of 11.5 g of sodium hydride (60% oil, 287 mmols) in 200 ml of dimethylformamide. The mixture was stirred for 1 hour, and 28.9 g (154 mmols) of 1,2-dibromoethane was added dropwise at room temperature. Then the mixture was stirred for 3 hours. To the reaction mixture were added 300 ml of water and 100 ml of ether, followed by stirring. The precipitated crystals were collected by filtration, giving 26.1 g of the title compound as colorless crystals (yield 60%).

後処理

  1. additionwere added dropwise
  2. stirringThen the mixture was stirred for 3 hours
  3. stirringby stirring
  4. filtrationThe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-a0543d76a26743c0a2a888f907e6d41f
出典データセット
uspto-grants-2004_03
特許番号
US06710062B1

関連ノート

読み込み中…