Dimethylformamide → 2,3-Dihydro-3-(4-ethoxycarbonylbut-1-yl)-4-methyl-2-oxo-1-pyrid-3-ylmethyleneamino-1H-imidazole
Reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6](=[O:17])[N:7]([N:9]=[CH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=1.Br[C:19](=[C:26]=O)[CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25].CN(C)C=[O:31]>>[CH2:24]([O:23][C:22]([CH2:21][CH2:20][CH2:19][CH2:26][N:5]1[C:4]([CH3:3])=[CH:8][N:7]([N:9]=[CH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:6]1=[O:17])=[O:31])[CH3:25]Participants
5
Reactant 4
Product 1
Procedure
0.72 g of sodium hydride are added to a suspension of 4.1 g of 2,3-dihydro-4-methyl-2-oxo-1-pyrid-3-ylmethyleneamino-1H-imidazole in 80 ml of N,N-dimethylformamide. The mixture is heated to 50°, treated with a solution of 5.22 g of 1-bromo-4-ethoxy-carbonyl-butane in 20 ml of N,N-dimethylformamide, and stirred for 30 minutes. The N,N-dimethylformamide is then removed on a rotary evaporator. The residue is treated with ethyl acetate, during which process sodium bromide precipitates. The mixture is filtered over Celite, and the filtrate is evaporated. The residue is treated with hexane, during which process crystals precipitate. The crystals are filtered off with suction and dried yielding the title compound melting at 74°-76°.
Workup
- temperatureThe mixture is heated to 50°
- customThe N,N-dimethylformamide is then removed on a rotary evaporator
- additionThe residue is treated with ethyl acetate, during which process sodium bromide
- customprecipitates
- filtrationThe mixture is filtered over Celite
- customthe filtrate is evaporated
- additionThe residue is treated with hexane, during which process crystals precipitate
- filtrationThe crystals are filtered off with suction
- customdried
Sources & evidence
- ORD record
- ord-9f87968347104a21b315c9bcbb925c1d
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05679623
Reaction notes
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