反応 #161346

反応方程式

2-aminobenzenethiol

2-acetoxymethyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid

oxalyl chloride

N,N-dimethylformamide

→

title compound

収率 117.5%

2-acetoxymethyl-5-(benzothiazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

収率 117.5%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他A 4-neck flask (500 mL) equipped with a reflux condenser
2. 2
   workup.ADDITIONwas then added dropwise at room temperature
3. 3
   温度to cool to room temperature
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   その他to give a pale yellow residue, which
6. 6
   workup.STIRRINGthis was stirred for 19 hours at 50° C
7. 7
   温度to cool to room temperature
8. 8
   ろ過after the precipitated crystals were filtered off
9. 9
   洗浄they were successively washed with distilled water
10. 10
    その他dried under reduced pressure
11. 11
    温度with heating

実験手順

A 4-neck flask (500 mL) equipped with a reflux condenser was charged with 2-acetoxymethyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid (5.98 g, 18.79 mmol), anhydrous tetrahydrofuran (158 mL), and oxalyl chloride (2.86 g, 22.50 mmol), and anhydrous N,N-dimethylformamide (1 mL) was then added dropwise at room temperature, after which the reaction mixture was stirred at 50° C. for 5 hours. After being allowed to cool to room temperature, the solvent was distilled off under reduced pressure to give a pale yellow residue, which was taken up in anhydrous tetrahydrofuran (100 mL), and then 2-aminobenzenethiol (2.35 g, 18.79 mmol) was added, and this was stirred for 19 hours at 50° C. This was allowed to cool to room temperature, and after the precipitated crystals were filtered off, they were successively washed with distilled water and dried under reduced pressure with heating to yield the title compound (9.00 g, quant.) as a white solid.

出典