Acetonitrile → HCID 178507542, compound

Participants

Reaction Conditions

Reaction Steps

Amino-phenylmercaptotetrazole (50.0 g, 0.258 mol) was stirred with triethylamine (38.2 mL, 0.274 mol) in 450 mL of dry acetonitrile at rt. After initial dissolution a white precipitate formed. Diethylcarbamyl chloride (35 mL, 0.274 mol) was dissolved in 50 mL of acetonitrile and added dropwise. The solution was then heated at reflux for 3 h. The solution was chilled in an ice bath and the precipitated triethylammonium chloride removed by filtration. The solution was concentrated at reduced pressure to yield an orange oil. This oil was filtered through a 250 g plug of silica gel using 2L of methylene chloride. The filtrate was concentrated at reduced pressure and 50 mL of methanol was added. The methanol solution was cooled to 0° C. and a white solid formed. The solid was collected, washed with ether, and dried to yield 40.3 g of the blocked 3-aminophenyltetrazole intermediate I12. ##STR115## 20. Preparation of intermediates I13 and I14.

Provenance & Evidence