Réaction #44916

Équation de réaction

oxalic acid

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

borane

Methanol

→

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

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source