Hydroxyamine hydrochloride → 4-[2-[2-Ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]benzaldehyde oxime

HRID 2211458Notes

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

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-3e96da7522d940ad8d85f2e507e64d03
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039266E1

Reaction notes

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