Dimethylformamide dimethyl acetal → HCID 66778357, compound
Reaction equation
[N:1]1([CH2:7][C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:15]OC(OC)N(C)C.Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1>C(O)C>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:15]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:33]2)=[CH:28][CH:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To methyl 4-(morpholin-4-yl)-3-oxobutanoate (7.0 g) synthesized in the above-mentioned (1) was added dimethylformamide-dimethylacetal (4.9 mL), and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, ethanol (200 mL) and 4-methoxyphenylhydrazine hydrochloride (6.3 g) were added, and the mixture was stirred at 100° C. for 3 hr. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (10.6 g, 93%) as a yellow oil.
Workup
- temperatureto cool to room temperature
- stirringthe mixture was stirred at 100° C. for 3 hr
- temperatureto cool to room temperature
- customthe solvent was evaporated under reduced pressure
- additionWater was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- concentrationThe extract was concentrated
- customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)
Sources & evidence
- ORD record
- ord-e56f9d67d3c54bd783c62f9dc3921b1d
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436043B2
Reaction notes
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