Acetic Acid → 2-(1,3-Benzothiazol-2-yl)acetonitrile

To a solution of malonitrile (6.61 g) and acetic acid (60 ml) in ethanol (100 ml) was added o-amino thio-phenol (7 ml) and the reaction was conducted at room temperature for 16 hours. This reaction mixture was diluted with ethyl acetate (200 ml) and washed with 5% aqueous sodium chloride solution. The organic layer was further washed with 3N NaOH (200 ml) and saturated NaCl solution (200 ml) and dried and the solvent was distilled off under reduced pressure. The residue was crystallized from IPE to give 2-benzothiazoleacetonitrile (13.8 g). This crystalline product (10.45 g) was dissolved in DMF (100 ml), and after addition of 60% sodium hydride (1.44 g) under ice-cooling, the solution was heated to 60° C. and stirred for 30 minutes. After cooling to room temperature, ethyl 6-bromohexanoate (5.31 ml) was added and the reaction was conducted at 60° C. for 30 minutes. After cooling to 10° C. or less, the reaction mixture was diluted with pure water (300 ml) and extracted with ethyl acetate (200 ml) twice. The pooled organic layer was washed with saturated aqueous sodium chloride solution and dried. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to provide ethyl 7-(benzothiazol-2-yl)-7-cyanoheptanoate (3.0 g).

1. washwashed with 5% aqueous sodium chloride solution
2. washThe organic layer was further washed with 3N NaOH (200 ml) and saturated NaCl solution (200 ml)
3. customdried
4. distillationthe solvent was distilled off under reduced pressure
5. customThe residue was crystallized from IPE

ORD record

ord-4b2c045350554b0f94efad39fadabcbd

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05804601