Sodium hydride → 4-allyl-2-(4-chlorobutyl)-5-(3-pyridyl)-1,2,4-triazol-3(2H,4H)-one
Reaction equation
[CH2:1]([N:4]1[C:8]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:7][NH:6][C:5]1=[O:15])[CH:2]=[CH2:3].[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]>CN(C)C=O>[CH2:1]([N:4]1[C:8]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:7][N:6]([CH2:19][CH2:20][CH2:21][CH2:22][Cl:23])[C:5]1=[O:15])[CH:2]=[CH2:3]Participants
Procedure
A solution of 4-allyl-5-(3-pyridyl)-1,2,4-triazol-3(2H,4H)-one (5 g) in dimethylformamide (50 ml) was added dropwise at ambient temperature under nitrogen to a stirred mixture of sodium hydride [0.92 g; 60% dispersion in mineral oil--pre-washed with petroleum ether (b.p. 40-60° C.)] and dimethylformamide (50 ml). The mixture was then stirred at ambient temperature for 1 hour, 1-bromo-4-chlorobutane (2.65 ml) was added, and stirring at ambient temperature was continued for 16 hours. The solvent was removed in vacuo, the residue was diluted with water (60 ml), and the product was extracted into ethyl acetate (2×200 ml). The extracts were dried (MgSO4), and the solvent was removed in vacuo to leave 4-allyl-2-(4-chlorobutyl)-5-(3-pyridyl)-1,2,4-triazol-3(2H,4H)-one as a yellow oil (6.93 g).
Workup
- stirringstirring at ambient temperature
- waitwas continued for 16 hours
- customThe solvent was removed in vacuo
- additionthe residue was diluted with water (60 ml)
- extractionthe product was extracted into ethyl acetate (2×200 ml)
- dry with materialThe extracts were dried (MgSO4)
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-8c514ba81af2471d9174a15f575721a8
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114334
Reaction notes
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