2-Chloro-2-methyl-3-nitrosobutane → 3,3,9,9-tetramethyl-6-[(2-nitro-1H-imidazol-1-yl)methyl]-5-oxa-4,8-diazaundecane-2,10-dione dioxime
Reaction equation
Cl[C:2]([CH3:8])([CH3:7])[CH:3]([N:5]=[O:6])[CH3:4].Cl.Cl.[NH2:11][CH2:12][CH:13]([O:23][NH2:24])[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[N+:20]([O-:22])=[O:21]>>[CH3:7][C:2]([CH3:8])([NH:24][O:23][CH:13]([CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[N+:20]([O-:22])=[O:21])[CH2:12][NH:11][C:2]([CH3:8])([CH3:7])[C:3](=[N:5][OH:6])[CH3:4])[C:3](=[N:5][OH:6])[CH3:4]Participants
Procedure
According to the General Reaction Scheme, N-(2,3-epoxypropyl)phthalimide (1) is reacted with 2-nitro-imidazole (2) to obtain 2-[2-Hydroxy-2-(2-nitro-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione (3). This product is then reacted with N-hydroxyphthalimide, preferably in the presence of a tertiary amine such as triphenylphosphine, to obtain the intermediate of Formula II, 2-{2-(1,3-dioxoisoindolin-2-yl)-1-[(2-nitroimidazolyl)methyl]ethoxy}isoindoline-1,3-dione (4). This intermediate is then reacted with hydrazine to obtain 1-[3-amino-2-(aminooxy)propyl]-2-nitro-1H-imidazole dihydrochloride (5), which is then reacted with the compound of Formula III to yield the compound of Formula I. A preferred compound of Formula III is 3-chloro-3-methyl-2-nitrosobutane, which, when used contacted with 1-[3-amino-2-(aminooxy)propyl]-2-nitro-1H-imidazole dihydrochloride (5), yields 3,3,9,9-tetramethyl-6-[(2-nitro-1H-imidazol-1-yl)methyl]-5-oxa-4,8-diazaundecane-2,10-dione dioxime (7).
Workup
- customto yield the compound of Formula I
Sources & evidence
- ORD record
- ord-d986145f82454b8aa87f93d92dd446d2
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06933391B2
Reaction notes
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