HCID 10022028, compound → 3,5-Dibutyl-1H-1,2,4-triazole
Reaction equation
[C:1]([N:20]1[CH:24]=[N:23][N:22]=N1)([C:14]1[CH:19]=[CH:18][CH:17]=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:25]([C:29]1N=C(Cl)N(CC2C=CC(C3C(C(O)=O)=CC=CC=3)=CC=2)N=1)[CH2:26][CH2:27]C>>[CH2:29]([C:24]1[N:20]=[C:1]([CH2:14][CH2:19][CH2:18][CH3:17])[NH:22][N:23]=1)[CH2:25][CH2:26][CH3:27]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) δ 0.88 (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-55bdf7d532aa451cb955b5345ba673b9
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05098920
Reaction notes
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