Methyl iodide → 3-(Cyanomethyl)-N,N-dimethyl-1H-indole-5-ethanesulphonamide

HRID 982008Notes

Reaction equation

HRID 982008 reaction equation
IC.CN([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH:14]=2)[NH:9][CH:8]=1)C.[C-:24]#[N:25].[K+]>CS(C)=O>[C:24]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([N:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])[CH:14]=2)[NH:9][CH:8]=1)#[N:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 134757383-[(Dimethylamino)methyl]-N,N-dimethyl-1H-indole-5-ethanesulphonamide

Product 1

HCID 134757623-(Cyanomethyl)-N,N-dimethyl-1H-indole-5-ethanesulphonamideYield 51.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Iodomethane (1.1 ml) was added to a stirred solution of the product of Stage (iii) (2.7 g) in dry dimethylsulphoxide (30 ml) and the resulting solution stirred at room temperature for 10 min. Potassium cyanide (2.7 g) was added, and the resulting mixture stirred at room temperature overnight. The mixture was partitioned between sodium carbonate, (2N, 300 ml) and ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil which was purified by `flash` chromatography (J, 5 cm col.) to give the title compound as a solid (1.3 g) m.p. 105°-107°.

Workup

  1. stirringthe resulting mixture stirred at room temperature overnight
  2. customThe mixture was partitioned between sodium carbonate, (2N, 300 ml) and ethyl acetate (2×100 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give an oil which
  6. customwas purified by `flash` chromatography (J, 5 cm col.)

Sources & evidence

ORD record
ord-598ebf8a9aef4c69b36c622c62aff7eb
Source dataset
uspto-grants-1991_02
Patent number
US04994483

Reaction notes

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