Potassium Hydroxide → 4,5-Diacetyl-[1,4,5]-oxadiazepine

HRID 1817777Notes

Reaction equation

[OH-].[K+].[C:3]([NH:6][NH:7][C:8](=[O:10])[CH3:9])(=[O:5])[CH3:4].[CH3:11][CH2:12][O:13][CH2:14][CH:15](Cl)Cl>CN(C)C=O>[C:3]([N:6]1[N:7]([C:8](=[O:10])[CH3:9])[CH:15]=[CH:14][O:13][CH:12]=[CH:11]1)(=[O:5])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

39.6 g of potassium hydroxide powder 85% (0.6 mol) are introduced into a mixture of 35 g of diacetylhydrazine (0.3 mol) and 560 ml of solvent (see Table 1). When the heat of reaction has died away, 85.8 g of 2,2-dichlorodiethyl ether (0.6 mol) are added; the reaction mixture is heated to 80° C. and maintained at 80-90° C. for 5 hours. The mixture is then cooled to 20° C. and filtered, and the filtration residue is washed with the solvent. The yield is given by the content of title compound in the combined filtrate. It will be seen that the solvents used according to the invention (tests 4-7) give far better yields of 4,5-diacetyl-[1,4,5]-oxadiazepine than N,N-dimethylformamide, which is known from the above prior art (DMFA, comparison test 8).

Workup

temperatureWhen the heat of reaction
temperaturemaintained at 80-90° C. for 5 hours
temperatureThe mixture is then cooled to 20° C.
filtrationfiltered
washthe filtration residue is washed with the solvent
customgive far better

Sources & evidence

ORD record: ord-49d7f6fdbc1545e7a7b36f289b6276b9
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598376B2

Reaction notes

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