Water → (ortho-[1-{4-chlorophenyl}-pyrazol-3-yl-oxymethyl]-phenyl)(5,6-dihydro-[1,4,2]dioxazin-3-yl)methanone O-methyl oxime

HRID 1280390Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([OH:13])=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16][O:17][N:18]=[C:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32]Cl)[C:20]1[O:25][CH2:24][CH2:23][O:22][N:21]=1.O>CN(C)C=O>[CH3:16][O:17][N:18]=[C:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][O:13][C:10]1[CH:11]=[CH:12][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]=1)[C:20]1[O:25][CH2:24][CH2:23][O:22][N:21]=1

Participants

Conditions

Temperature: 22.5 °C

Procedure

A solution of 0.97 g of 1-(para-chlorophenyl)-3-hydroxypyrazole in 20 ml of anhydrous dimethylformamide (DMF) was admixed with 0.13 g of sodium hydride and then stirred at 20-25 ° C. for approximately one hour. 1.34 g of the oxime from Example 2 were then added and the mixture was stirred at 60° C. for approximately three hours and then at 20-25° C. for approximately 14 hours. 300 ml of water were added and the mixture was then extracted with methyl tert-butyl ether (MTBE). The combined organic phases were washed with water and dried, and the solvent was then removed. The residue was chromatographed over silica gel (cyclohexane/ethyl acetate mixture [1:1]), giving 1.15 g of the title compound as a light-beige amorphous powder of m.p. 56-59° C.

Workup

stirringthe mixture was stirred at 60° C. for approximately three hours
waitat 20-25° C. for approximately 14 hours
extractionthe mixture was then extracted with methyl tert-butyl ether (MTBE)
washThe combined organic phases were washed with water
customdried
customthe solvent was then removed
customThe residue was chromatographed over silica gel (cyclohexane/ethyl acetate mixture [1:1])

Sources & evidence

ORD record: ord-5f626f04bd844732a99c55e1c376bacb
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451790B1

Reaction notes

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