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

HRID 1817778
Notes
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Reaction equation

HRID 1817778 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:15][CH2:16][O:17][CH2:18][CH:19](Cl)Cl>CS(C)=O>[C:1]([N:4]1[N:5]([C:6](=[O:8])[CH3:7])[CH:19]=[CH:18][O:17][CH:16]=[CH:15]1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72884Acetic acid, 2-acetylhydrazideHCID 139875142,2-Dichlorodiethyl Ether

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 35 g of diacetylhydrazine (0.3 mol), 124.4 g or 165.8 g of ground potassium carbonate (0.9 or 1.2 mol, respectively), 85.8 g of 2,2-dichlorodiethyl ether (0.6 mol) and 560 ml of solvent (see Table 2) is heated to 125° C. and maintained at 125-130° C. or 80-90° C. (in the case of DMSO) 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.

Workup

  1. filtrationfiltered
  2. washthe filtration residue is washed with the solvent

Sources & evidence

ORD record
ord-3eddec40a65242c0868f7faf96b798b2
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07598376B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes