1-methyl-1H-indol-5-amine → 5-isothiocyanato-1-methyl-1H-indole

HRID 76099

Reaction equation

HRID 76099 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.[C:12](C1NC=CN=1)(C1NC=CN=1)=[S:13]>C(OCC)(=O)C>[N:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2)=[C:12]=[S:13]

Participants

4

Reactant 2

HCID 27695641-methyl-1H-indol-5-amineHCID 11412697Thiocarbonyl diimidazole

Product 1

HCID 866216825-isothiocyanato-1-methyl-1H-indoleYield 78.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A flask was charged with 5-amino-1-methyl-1H-indole (8.8 g; 60 mmol), thiocarbonyl diimidazole (10.7 g; 60 mmol) and ethyl acetate (200 mL). The reaction was heated at 50° C. for five minutes, and after cooling, the solvent was evaporated. The crude material was dissolved in dichloromethane (100 mL) and filtered through a short plug of silica gel, which was washed with another bolus of dichloromethane (100 mL). The organic eluent was evaporated to give 5-isothiocyanato-1-methyl-1H-indole (8.9 g; 47 mmol).

Workup

  1. temperatureafter cooling
  2. customthe solvent was evaporated
  3. dissolutionThe crude material was dissolved in dichloromethane (100 mL)
  4. filtrationfiltered through a short plug of silica gel, which
  5. washwas washed with another bolus of dichloromethane (100 mL)
  6. customThe organic eluent was evaporated

Sources & evidence

ORD record
ord-863637f6655745558c37dbc39ba37621
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Linked notes

Loading…