Dimethylformamide → 6-ethylsulfanyl-1H-indole-3-carbonitrile

HRID 502290Notes

Reaction equation

HRID 502290 reaction equation
[CH2:1]([S:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)[CH3:2].[CH3:13][N:14](C=O)C>>[CH2:1]([S:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 226127886-ethylsulfanyl-1H-indole

Product 1

HCID 594261306-ethylsulfanyl-1H-indole-3-carbonitrileYield 84%

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-ethylsulfanyl-1H-indole (2.75 g, 15.54 mmol) in DMF (20 mL) was added chlorosulfonyl isocyante dropwise at −30° C. The temperature was raised to 0° C. after addition and stirred for 30 minutes. The mixture was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried over Mg2SO4, concentrated and purified on silica gel (CH2Cl2) to provide 6-ethylsulfanyl-1H-indole-3-carbonitrile (3.25 g, 84%) as a white solid.

Workup

  1. additionwas added chlorosulfonyl isocyante dropwise at −30° C
  2. additionafter addition
  3. customThe mixture was partitioned between EtOAc and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Mg2SO4
  6. concentrationconcentrated
  7. custompurified on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-1d924ace576949848a448ef59614479f
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

Loading…