Réaction #5922

Équation de réaction

oxalic acid

2-(4-chlorophenyl)-4-(N-methylaminoacetyl)-3,4-dihydro-2H-1,4-benzothiazine

allyl bromide

potassium carbonate

→

4-(N-allyl-N-methylaminoacetyl)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine oxalate

Solvants

water

dimethylformamide

ether

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture is extracted with ethyl acetate
2. 2
   workup.DISTILLATIONAfter the solvent is distilled off
3. 3
   Autrethe residue is purified by silica gel column chromatography (solvent, chloroform:methanol=40:1)
4. 4
   AutreThe caramel thus obtained
5. 5
   LavageThe resulting precipitate is washed with ether
6. 6
   Autredried

Mode opératoire

A mixture of 2-(4-chlorophenyl)-4-(N-methylaminoacetyl)-3,4-dihydro-2H-1,4-benzothiazine (1.80 g), allyl bromide (0.52 ml), potassium carbonate (2.25 g) and dimethylformamide (20 ml) is stirred at room temperature for 3.5 hours. The reaction mixture is poured into water, and the mixture is extracted with ethyl acetate. After the solvent is distilled off, the residue is purified by silica gel column chromatography (solvent, chloroform:methanol=40:1). The caramel thus obtained is dissolved in ether and thereto is added 1.1 equivalent of oxalic acid. The resulting precipitate is washed with ether and dried to give 4-(N-allyl-N-methylaminoacetyl)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine oxalate as powder.

Source