Pyridine → 2-Chloro-4-methoxyphenoxy-1,3-thiazole-5-carbaldehyde oxime

HRID 404898Notes

Reaction equation

[Cl:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[S:6][C:7]([CH:10]=O)=[CH:8][N:9]=1.N1C=CC=CC=1.Cl.[NH2:25][OH:26]>O>[Cl:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[S:6][C:7]([CH:10]=[N:25][OH:26])=[CH:8][N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of Example 30B (13.05 g, 48.4 mmol) in pyridine (38.8 g, 484 mmol) was added hydroxylamine hydrochloride (33.7 g, 484 mmol). The mixture was heated at 80° C. for 0.5 hours, cooled to ambient temperature, treated with water (1000 mL) and filtered. The collected solids were dried in a vacuum oven to provide 13.2 g of the title compound (96%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.82 (s, 3H) 7.03 (dd, J=9.01, 3.13 Hz, 1H) 7.25 (d, J=2.94 Hz, 1H) 7.52 (d, J=8.82 Hz, 1H) 7.68 (s, 1H) 7.81 (s, 1H) 12.02 (s, 1H); MS (ESI) m/z 284.9 (M+H)+.

Workup

temperaturecooled to ambient temperature
filtrationfiltered
customThe collected solids were dried in a vacuum oven

Sources & evidence

ORD record: ord-e6c0911bc190451fa274289cefaac7b7
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748627B2

Reaction notes

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