Formaldehyde → HCID 15065517, compound
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10].[CH2:11]=O.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]#[C:9][CH2:11][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:3]1=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The intermediate imidazolidinones and imidazolones were converted to the final products using the general procedures outlined in Scheme 2. 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-imidazol-2-one was reacted with paraformaldehyde and pyrrolidine in dioxane using cuprous chloride as catalyst to give 1,3-dihydro-1-methyl-3-[4-(1-pyrrolidinyl)-2-butynyl]-2H-imidazol-2-one. The diethylamine analogue was prepared similarly and was reacted with cyanogen bromide to give the bromide XI which was reacted with imidazole to give 1,3-dihydro-1-[4-(1H-imidazol-1-yl)-2-butynyl]-3-methyl-2H-imidazol-2-one and with 1-acetyl-4-methylimidazole to give XII which was hydrolyzed to 1,3-dihydro-1-methyl-3-[4-(5-methyl-1H-imidazol-1-yl)-2-butynyl]-2H-imidazol-2-one. The imidazolidinone analogues of Table 1, imidazolones of Table 2 and imidazolidinedione and tetrahydropyrimidinones of Table 3 were prepared by these general procedures.
Sources & evidence
- ORD record
- ord-94c512e74b2b4048a1aed464e71a6199
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137905
Reaction notes
Loading…