Indole → 3-(methylthio)-1H-indole

HRID 1947065ノート

反応式

HRID 1947065 の反応式
[S:1]([CH3:3])[CH3:2].ClN1C(=O)CCC1=O.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)C=[CH:13]1.CCOCC>C(Cl)Cl>[CH3:2][S:1][C:3]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][CH:13]=1

参加物

6

反応物 4

HCID 798IndoleHCID 1068Dimethyl SulfideHCID 3283Diethyl EtherHCID 31398Chlorosuccinimide

生成物 1

HCID 108882523-(methylthio)-1H-indole収率 98.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
100 °C

実験手順

Me2S (955 μL, 13 mmol) was added to a solution of N-chlorosuccinimide (NCS, 1.47 g, 11 mmol) in DCM (80 mL) at 0° C., and stirred under N2 for 35 min. A solution of indole (1.17 g, 10 mmol) in DCM was added slowly, stirring at 0° C. for 2 h. While still cold, Et2O was added, and the white gum that formed was filtered off, dried under vacuum for 1.5 h, and stored at RT overnight. The intermediate was dissolved in DMSO, and the mixture heated to 100° C. under vacuum for 25 min. The product was poured into water, extracted with Et2O, and concentrated to dryness to yield 3-methylsulfanyl-1H-indole (1.609 g, 98.6% yield).

後処理

  1. stirringstirring at 0° C. for 2 h
  2. customthe white gum that formed
  3. filtrationwas filtered off
  4. customdried under vacuum for 1.5 h
  5. waitstored at RT overnight
  6. dissolutionThe intermediate was dissolved in DMSO
  7. additionThe product was poured into water
  8. extractionextracted with Et2O
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-cc063adc5c9640319a1b2129781a3176
出典データセット
uspto-grants-2013_03
特許番号
US08399462B2

反応ノート

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