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1207615-07-3

9H-Imidazo[4,5-c]tetrazolo[1,5-a]pyridine synthesis

2synthesis methods
14432-13-4 Synthesis
2-CHLORO-4-N-NITRO(AMINOPYRIDINE)

14432-13-4
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143314-16-3 Synthesis
1-Ethyl-3-methylimidazolium tetrafluoroborate

143314-16-3
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9H-Imidazo[4,5-c]tetrazolo[1,5-a]pyridine

1207615-07-3
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Yield:1207615-07-3 98%

Reaction Conditions:

with lithium azide in water;N,N-dimethyl-formamide at 20 - 80; for 6 h;Product distribution / selectivity;

Steps:



To a suspension solution of compound 7 (4.20 g, 27.35 mmol) in 20 mL of DMF-[emim]BF4 (10:1 v/v), LiN3 (28 mL, 20 wt % in H2O) was added at room temperature and the reaction mixture was heated at 80 °C for 6 h. The mixture was concentrated under reduced pressure followed by the residue was treated with acetone (20 mL). The result solid was filtered, washed with acetone (10 mL x 3) and dried under reduced pressure for 24 h to give a white solid (4.35 g, 26.80 mmol) in 98 % yield, mp 205-207 0C; UV (H2O) λmax 271.0 (ε 5134 pH 2); 1H-NMR (DMSO-J6, 500 MHz) δ 9.07 (d, J= 7.0 Hz5 IH), 8.56 (s, IH), 7.71 (d, J= 7.0 Hz, IH); 13C-NMR (DMSO-J6, 125 MHz) δ 144.06, 143.83, 134.99, 125.67, 121.22, 106.93; IR (neat) 3074, 2928, 2854, 2361, 1647, 1523 cm-1; HRMS (ES) calcd for C6H4N6 (M+H+) 161.0576, found 161.0538.

References:

WO2007/47793,2007,A2 Location in patent:Page/Page column 89-90