(5-chloro-1H-benzo[d]imidazol-2-yl)methanol synthesis
- Product Name:(5-chloro-1H-benzo[d]imidazol-2-yl)methanol
- CAS Number:6953-65-7
- Molecular formula:C8H7ClN2O
- Molecular Weight:182.61
79-14-1
95-83-0
6953-65-7
a) A mixture of 4-chloro-1,2-benzenediamine (105 g, 736 mmol, 1 eq.) and ethanoic acid (112 g, 2 eq.) in xylene (1500 mL) was stirred and refluxed at 150 °C for 4 h. The reaction was carried out with the addition of 3N hydrochloric acid (480 mL). Upon completion of the reaction, the reaction solution was cooled to 60 °C and acidified by slow addition of 3N hydrochloric acid (480 mL), followed by adjusting the pH with ammonia to 7-8. The reaction mixture was filtered and the solid product was collected and washed with water and tert-butyl methyl ether sequentially to afford 123 g of (6-chloro-1H-benzimidazol-2-yl)methanol in 82% yield.
Yield:6953-65-7 82%
Reaction Conditions:
in 5,5-dimethyl-1,3-cyclohexadiene at 150; for 4 h;
Steps:
Step 1: synthesis of (5-chloro-1H-benzo[djimidazol-2-yl)methanol (intermediate21 a)
21 a)A mixture of 4-chlorobenzene-1,2-diamine (105 g, 736 mmoles, 1 eq.) andhydroxyacetic acid (112 g, 2 eq.) in xylene (1500 mL) was stirred at 150 °C for 4 hours. The mixture was then cooled to 60 °C and treated with 3N HC1 (480 ml), then basified to pH=7-8 by the addition of aqueous ammonia. The mixture was filtered and the solid was collected, washed with H20 and tert-butyl methyl ether to give 123 g (82% yield) of (5 -chloro- 1 H-benzo [d]imidazo l-2-yl)methano 1 21 a.
References:
WO2014/60411,2014,A1 Location in patent:Page/Page column 58