Reacción #44916

Ecuación de reacción

oxalic acid

2-(1H-Indol-3-ylsulfanyl)-N,N-dimethyl benzamide

borane

Methanol

→

[2-(1H-Indol-3-ylsulfanyl)benzyl]dimethyl amine

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 30 min
2. 2
   Otroevaporated in vacuo
3. 3
   workup.DISSOLUTIONThe mixture was redissolved in ethyl acetate (100 mL)
4. 4
   Lavadowashed with saturated sodium hydrogen carbonate (20 mL)
5. 5
   Secadodried over anhydrous MgSO4
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe product was crystallized as an oxalate salt by dissolution in acetone

Procedimiento

2-(1H-Indol-3-ylsulfanyl)-N,N-dimethyl benzamide (1 mmol) was dissolved in dry tetrahydrofuran (30 mL). To the mixture was added 3 mL 1 M borane in tetrahydrofuran and the mixture was stirred at room temperature for 24 hours. Methanol (5 mL) was added and the mixture stirred at room temperature for 30 min and then evaporated in vacuo. The mixture was redissolved in ethyl acetate (100 mL) and washed with saturated sodium hydrogen carbonate (20 mL), dried over anhydrous MgSO4 and evaporated in vacuo. The product was crystallized as an oxalate salt by dissolution in acetone and addition of one equivalent of oxalic acid.

Fuente