Sodium Azide → HCID 15295111, compound

HRID 726722Notes

Reaction equation

[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[N:10]([CH2:21][CH2:22][CH2:23]Cl)[N:9]=1.[N-:34]=[N+]=[N-].[Na+]>CN(C=O)C.O>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[N:10]([CH2:21][CH2:22][CH2:23][NH2:34])[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-(3,5-Bis(trifluoromethyl)phenethyl)-4-benzyl-1-(3-chloropropyl)-5-oxo-1,2,4-triazole (Description 2, 2.5 g, 0.005 mol) was dissolved in DMF (30 ml) and sodium azide (0.495 g, 0.0076 mol) added and the reaction heated to 80° C. for 16 hours. The reaction was cooled, diluted with water (50 ml) and extracted into ethyl acetate (75 ml). The organic layer was washed with water (3×25 ml), brine and dried (MgSO4). The solvent was removed and the resulting azide (colourless off) was dissolved in ethanol (30 ml) and hydrogenated over palladium hydroxide (0.300 g) at 50 psi for 4 hours. The catalyst was filtered and the solvent removed in vacuo to furnish the title compound as a colourless oil. (2.4 g).

Workup

temperatureThe reaction was cooled
extractionextracted into ethyl acetate (75 ml)
washThe organic layer was washed with water (3×25 ml), brine
dry with materialdried (MgSO4)
customThe solvent was removed
dissolutionthe resulting azide (colourless off) was dissolved in ethanol (30 ml) and hydrogenated over palladium hydroxide (0.300 g) at 50 psi for 4 hours
filtrationThe catalyst was filtered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-0a02b46007624c84a6cdc2071052f070
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710161

Reaction notes

Loading…