Réaction #1869158

Équation de réaction

5-amino-3-(2-dimethylaminoethyl)-1H-indol

5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride

→

N-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-5-chloro-3-methyl-benzo[b]thiophene-2-sulphonamide

Rendement 82.0%

Solvants

pyridine

pyridine

Conditions de réaction

Traitement

1. 1
   AutreIt is then evaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in ethyl acetate
3. 3
   LavageThe organic phase is washed with water
4. 4
   Autrea saturated solution of sodium bicarbonate, it is separated
5. 5
   Séchagedried with anhydrous sodium sulphate
6. 6
   AutreThe organic solution is evaporated to dryness
7. 7
   Lavagethe resulting solid is repeatedly washed with ethyl ether

Mode opératoire

To a solution of 3.05 g (15 mMol) of 5-amino-3-(2-dimethylaminoethyl)-1H-indol in 100 ml of pyridine is added dropwise at ambient temperature a solution of 4.21 g (15 mMol) of 5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride in 20 ml of pyridine. The reaction mixture is stirred at ambient temperature for 20 hours. It is then evaporated to dryness, slightly alkalinised with diluted ammonia and dissolved in ethyl acetate. The organic phase is washed with water and a saturated solution of sodium bicarbonate, it is separated and dried with anhydrous sodium sulphate. The organic solution is evaporated to dryness and the resulting solid is repeatedly washed with ethyl ether, to yield 5.5 g (82%) of N-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-5-chloro-3-methyl-benzo[b]thiophene-2-sulphonamide as a solid with m.p.=226-227° C.

Source