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

HRID 1817775Notes

Reaction equation

HRID 1817775 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>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

5

Reactant 3

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

Product 1

HCID 673358624,5-Diacetyl-[1,4,5]-oxadiazepineYield 78.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
82.5 °C

Procedure

10.6 g of finely pulverised 85% potassium hydroxide are introduced into a solution of 9.3 g of N,N′-diacetylhydrazine and 141 g of dimethyl sulfoxide in such a manner that a temperature of 33° C. is not exceeded. After heating to 80 to 85° C., 23 g of 2,2′-dichlorodiethyl ether are added dropwise to the reaction mixture over the course of 50 minutes. The resulting highly fluid suspension is maintained at 80 to 85° C. for 3 hours, then cooled to 20 to 25° C. and filtered, and the filtration residue is washed with dimethyl sulfoxide. 11.4 g (76.0%) of 4,5-diacetyl-[1,4,5]-oxadiazepine are obtained from the combined filtrates by concentration by evaporation.

Workup

  1. temperatureThe resulting highly fluid suspension is maintained at 80 to 85° C. for 3 hours
  2. temperaturecooled to 20 to 25° C.
  3. filtrationfiltered
  4. washthe filtration residue is washed with dimethyl sulfoxide

Sources & evidence

ORD record
ord-37d6fbc9fc80427a9f467d10f4be6b67
Source dataset
uspto-grants-2009_10
Patent number
US07598376B2

Reaction notes

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