HCID 10321302, compound → 3,5-Dibutyl-1H-1,2,4-triazole
Reaction equation
C(N1C=NN=N1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:25]([C:29]1[N:33](CC2C=CC(C3C(C(O)=O)=CC=CC=3)=CC=2)[N:32]=[C:31]([C:50]([CH:52]2CCC[CH2:54][CH2:53]2)=O)[N:30]=1)[CH2:26][CH2:27][CH3:28]>>[CH2:50]([C:31]1[N:30]=[C:29]([CH2:25][CH2:26][CH2:27][CH3:28])[NH:33][N:32]=1)[CH2:52][CH2:53][CH3:54]Participants
Procedure
A solution of 64.5 g (0.50 mol) of ethyl iminovalerate [P. Reynaud and R. C. Moreau, Bull. Soc. Chim. France, 2997 (1964)] in 100 mL of methanol was added slowly to 58.0 g (0.50 mol) of valeric acid hydrazide (Lancaster Synthesis) in 400 mL of methanol at 0° C. under a nitrogen atmosphere. After the addition was complete, the reaction was allowed to warm to ambient temperature and then stir at reflux for 2 days. The solvent was removed in vacuo; purification by silica gel chromatography (Waters Prep-500A) using ethyl acetate/hexane (80:20) gave 78.9 g (93%) of a colorless solid: mp 50.5°-51.5° C.; NMR (CDCl3) δ0.88 (t, J=7 Hz, 6H), 1.28-1.33 (m, 4H), 1.63-1.77 (m, 4H), 2.72 (t, J=7 Hz, 4H); MS (FAB) m/e (rel intensity) 183 (12%), 182 (100), 181 (3), 180 (6), 152 (8), 139 (4); HRMS. Calcd for M+H: 182.1657. Found: 182.1661.
Sources & evidence
- ORD record
- ord-b05b0f2ac59d443fa8787f080b57871e
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05217985
Reaction notes
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