Phosphorus oxychloride → 2-chloro-6-methyl-1H-1,3-benzodiazole

5-Methyl-1,3-dihydro-2H-benzimidazol-2-one (13.1 g, 88.5 mmol) and phosphorus oxychloride (130 ml, freshly distillated) was charged into three-neck round-bottom flask. The mixture was heated up to boiling point till homogeneous solution was formed. After that the dried hydrogen chloride was bubbled through inlet gas-pipe into the reaction mixture. The mixture was boiled for 15 hours. Excess of phosphorus oxychloride was distillated in vacuo. Mixture of ice and water (250 ml) was added to residue. The obtained suspension was cooled to the room temperature and filtered. Filtrate was alkalinized by aqueous ammonia solution till pH 8, cooled by cold water and filtered crude 2-chloro-6-methyl-1H-benzimidazole. White powder was crystallized from aqueous methanol (water-methanol: 1:1, 200 ml), washed by aqueous methanol and dried in a desiccator under phosphorous oxide in vacuo. Yield: 8.17 g (55%).

1. temperatureThe mixture was heated up
2. customwas formed
3. customAfter that the dried hydrogen chloride was bubbled through inlet gas-pipe into the reaction mixture
4. additionMixture of ice and water (250 ml)
5. additionwas added to residue
6. filtrationfiltered
7. temperaturecooled by cold water
8. filtrationfiltered crude 2-chloro-6-methyl-1H-benzimidazole
9. customWhite powder was crystallized from aqueous methanol (water-methanol: 1:1, 200 ml)
10. washwashed by aqueous methanol
11. customdried in a desiccator under phosphorous oxide in vacuo

ORDレコード

ord-0e9dc062fefe49adaf012e64e057b7ca

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08142863B2