Indole → 3-methylsulfanyl-1H-indole

HRID 1947065Notes

Reaction equation

HRID 1947065 reaction equation
[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

Participants

6

Reactant 4

HCID 798IndoleHCID 1068Dimethyl SulfideHCID 3283Diethyl EtherHCID 31398Chlorosuccinimide

Product 1

HCID 108882523-methylsulfanyl-1H-indoleYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cc063adc5c9640319a1b2129781a3176
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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