Water → 2-[(5,6-Dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzaldehyde

HRID 2229129Notes

Reaction equation

C[N+]1([O-])CC[O:5]CC1.[CH3:9][O:10][N:11]=[C:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]Cl)[C:13]1[O:18][CH2:17][CH2:16][O:15][N:14]=1.O>CN(C)C=O>[O:15]1[CH2:16][CH2:17][O:18][C:13]([C:12](=[N:11][O:10][CH3:9])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH:25]=[O:5])=[N:14]1

Participants

Conditions

Temperature: 120 °C

Procedure

19.5 g (0.14 mol) of N-methylmorpholine N-oxide are added to a solution of 15 g (0.056 mol) of (2-chloromethyl-phenyl)-(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methanone O-methyl oxime in 150 ml of dimethylformamide and the mixture is stirred at 120° C. for 2 hours. After cooling, the mixture is poured into 1000 ml of water and extracted three times with 200 ml of ethyl acetate each time. The combined organic phases are dried over magnesium sulphate and concentrated under reduced pressure. The residue is stirred with diisopropyl ether and the solid formed is filtered off with suction. 10.5 g (76% of theory) of 2-[(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzaldehyde are obtained.

Workup

temperatureAfter cooling
extractionextracted three times with 200 ml of ethyl acetate each time
dry with materialThe combined organic phases are dried over magnesium sulphate
concentrationconcentrated under reduced pressure
stirringThe residue is stirred with diisopropyl ether
customthe solid formed
filtrationis filtered off with suction

Sources & evidence

ORD record: ord-55ce8ac9ef244f81b2349ddb2fb10a33
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420362B1

Reaction notes

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