Bis(2-chloroethyl) ether → 4,5-Diacetyl-[1,4,5]-oxadiazepine

HRID 1817776Notes

Reaction equation

HRID 1817776 reaction equation
[OH-].[K+].[C:3]([NH:6][NH:7][C:8](=[O:10])[CH3:9])(=[O:5])[CH3:4].[CH2:11]([O:14][CH2:15][CH2:16]Cl)[CH2:12]Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.CS(C)=O>[C:3]([N:6]1[N:7]([C:8](=[O:10])[CH3:9])[CH:16]=[CH:15][O:14][CH:11]=[CH:12]1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 72884Acetic acid, 2-acetylhydrazide

Product 1

HCID 673358624,5-Diacetyl-[1,4,5]-oxadiazepine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

105.6 g of finely pulverised potassium hydroxide are introduced into a solution of 92.9 g of N,N′-diacetylhydrazine and 1410 g of dimethyl sulfoxide. When the heat of reaction has died away, 229.9 g of 2,2′-dichlorodiethyl ether are added and then 221.1 g of finely ground potassium carbonate are introduced. The reaction mixture is heated to 70° C. and maintained at 70 to 75° C. for 2 hours, then cooled to 20 to 25° C. and filtered, and the filtration residue is washed with dimethyl sulfoxide. Concentration of the combined filtrates by evaporation yields an oil, to which 157 g of isopropanol are added. After cooling to −10° C., filtration is carried out and the crystalline residue is washed with isopropanol. After drying of the residue, 99.4 g (65.1%) of 4,5-diacetyl-[1,4,5]-oxadiazepine are obtained in a purity of 97.6%.

Workup

  1. temperatureWhen the heat of reaction
  2. temperaturemaintained at 70 to 75° C. for 2 hours
  3. temperaturecooled to 20 to 25° C.
  4. filtrationfiltered
  5. washthe filtration residue is washed with dimethyl sulfoxide
  6. customConcentration of the combined filtrates by evaporation
  7. customyields an oil
  8. temperatureAfter cooling to −10° C.
  9. filtrationfiltration
  10. washthe crystalline residue is washed with isopropanol
  11. dry with materialAfter drying of the residue, 99.4 g (65.1%) of 4,5-diacetyl-[1,4,5]-oxadiazepine
  12. customare obtained in a purity of 97.6%

Sources & evidence

ORD record
ord-e8d9a34ada084e4b885556bc4f1c960c
Source dataset
uspto-grants-2009_10
Patent number
US07598376B2

Reaction notes

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