Acetonitrile → HCID 178507542, compound

Temperature

0 °C

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.

1. dissolutionAfter initial dissolution a white precipitate
2. customformed
3. additionadded dropwise
4. temperatureThe solution was then heated
5. temperatureat reflux for 3 h
6. temperatureThe solution was chilled in an ice bath
7. customthe precipitated triethylammonium chloride removed by filtration
8. concentrationThe solution was concentrated at reduced pressure
9. customto yield an orange oil
10. filtrationThis oil was filtered through a 250 g plug of silica gel using 2L of methylene chloride
11. concentrationThe filtrate was concentrated at reduced pressure and 50 mL of methanol
12. additionwas added
13. customa white solid formed
14. customThe solid was collected
15. washwashed with ether
16. customdried

ORD record

ord-687db36518c345e9a890003957c38299

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05994051