Indole → 3-(methylthio)-1H-indole

HRID 1947065노트

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HRID 1947065 반응식
[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

참가 물질

6

반응물 4

HCID 798IndoleHCID 1068Dimethyl SulfideHCID 3283Diethyl EtherHCID 31398Chlorosuccinimide

생성물 1

HCID 108882523-(methylthio)-1H-indole수율 98.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cc063adc5c9640319a1b2129781a3176
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399462B2

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