Iodoethane → N11-Ethyl-N5-methyl-5,11-dihydro-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
Reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[N:15][C:8]=2[NH:7][C:6]2[N:16]=[CH:17][CH:18]=[CH:19][C:5]1=2.[H][H].[CH2:22](I)[CH3:23]>CN(C)C=O.O>[CH2:22]([N:7]1[C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10](=[O:11])[N:4]([CH3:3])[C:5]2[CH:19]=[CH:18][CH:17]=[N:16][C:6]1=2)[CH3:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2.00 g of a 50% dispersion of sodium hydride in mineral oil was added to a solution of 5.75 g (0.025 mol) of 5,11-dihydro-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one in 100 ml of dimethylformamide. When the evolution of hydrogen ceased, the mixture was heated to 50° C. for 30 min. and then cooled to room temperature. Then, 7.80 g of ethyl iodide (neat) was added dropwise over 15 minutes, and the resulting mixture was allowed to stir overnight at room temperature. The excess sodium hydride was decomposed by the careful addition of ice, followed by water. The product was extracted with ether, dried (anhydrous sodium sulfate), and evaporated to yield 4.5 g (70% of theory) of 5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, m.p. 130°-132° C.
Workup
- temperaturecooled to room temperature
- extractionThe product was extracted with ether
- dry with materialdried (anhydrous sodium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-ca1957c2ce14473c88f335c2c693d765
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05366972
Reaction notes
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