Hydroxyamine hydrochloride → 4-[2-[2-Ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde oxime
Reaction equation
Cl.[NH2:2][OH:3].O.O.O.C([O-])(=O)C.[Na+].[CH2:12]([C:14]1[N:15]([CH2:22][CH2:23][O:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[C:16](=[O:21])[CH:17]=[C:18]([CH3:20])[N:19]=1)[CH3:13]>O.C(O)C>[CH2:12]([C:14]1[N:15]([CH2:22][CH2:23][O:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[N:2][OH:3])=[CH:27][CH:26]=2)[C:16](=[O:21])[CH:17]=[C:18]([CH3:20])[N:19]=1)[CH3:13]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
To a stirred solution of hydroxylamine hydrochloride (10.0 g, 143.0 mmol) and sodium acetate trihydrate (20.0 g, 146.9 mmol) in water (100 ml) at 30° C. was added a hot solution of 4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde (5.72 g, 20.0 mmol) (obtained from preparation 3) in ethanol (100 ml). The reaction mixture was immersed in a preheated oil bath (95° C.) and refluxed for 3 h. The reaction mixture was then cooled to room temperature and concentrated to a volume where crystals of oxime started separating out and the mixture was kept aside for 30 min. to 1 h at 25° C. The resultant crystals were filtered and washed with water and dried to obtain the title compound (5.42 g, 90%).
Workup
- customThe reaction mixture was immersed in a preheated oil bath
- temperatureThe reaction mixture was then cooled to room temperature
- concentrationconcentrated to a volume where crystals of oxime
- customstarted separating out and the mixture
- waitwas kept aside for 30 min. to 1 h at 25° C
- filtrationThe resultant crystals were filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-4dbb9d1514004399a11df0957e36f8b6
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310069B1
Reaction notes
Loading…