تفاعل #220882

معادلة التفاعل

Tributyltin azide

3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

→

tetrazole

3,5-bis(benzyloxy)-N-[5-(1H-tetraazol-5-yl)pyridin-2-yl]benzamide

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةat reflux for 16 hours
3. 3
   درجة الحرارةThe suspension was cooled
4. 4
   أخرىpartitioned between ethyl acetate and hydrochloric acid (1M)
5. 5
   تركيزThe organic layer was concentrated in vacuo
6. 6
   أخرىthe residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM)

الإجراء التجريبي

Tributyltin azide (156 μL, 0.57 mmol) was added to a suspension of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (180 mg, 0.41 mmol) in toluene (3 mL). The mixture was heated at reflux for 16 hours. The suspension was cooled and partitioned between ethyl acetate and hydrochloric acid (1M). The organic layer was concentrated in vacuo and the residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM). The tetrazole was obtained as a colourless solid (113 mg, 57%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 6.88 (1H, s); 7.26-7.48 (12H, m); 8.40 (1H, d); 8.46 (1H, dd); 9.04 (1H, s); 11.13 (1H, br s); m/z (LCMS; ESI+) 479 (MH+).

المصدر