Methanesulfonyl chloride → N-[2-(1H-Indol-5-yl)ethyl]methanesulphonamide

HRID 1087409Notes

Reaction equation

HRID 1087409 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][NH2:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][NH:12][S:14]([CH3:13])(=[O:16])=[O:15])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 172211022-(1H-Indol-5-yl)ethan-1-amine

Product 1

HCID 19817119N-[2-(1H-Indol-5-yl)ethyl]methanesulphonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1H-indole-5-ethanamine (1.00 g), methane sulphonylchloride (0.69 ml), 8% sodium bicarbonate solution (100 ml) and ethyl acetate (100 ml) were stirred vigorously for 20 min. The organic phase was separated and the aqueous phase extracted with ethyl acetate (50 ml). The combined organic phases were dried and evaporated in vacuo to give the title compound as an oil (1.50 g). T.l.c. SiO2, EtOAc Rf 0.8

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase extracted with ethyl acetate (50 ml)
  3. customThe combined organic phases were dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b0c49db82bb143bcbbd10bab183ebc9e
Source dataset
uspto-grants-1991_07
Patent number
US05036078

Reaction notes

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