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Potassium Carbonate → 5-(4-Chloro-phenyl)-3-(4-nitro-benzyl)-3,6-dihydro-[1,3,4]oxadiazin-2-one

HRID 44289
Notes
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Reaction equation

HRID 44289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][O:12][C:11](=[O:14])[NH:10][N:9]=2)=[CH:4][CH:3]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][O:12][C:11](=[O:14])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[N:9]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 133659155-(4-Chlorophenyl)-3,6-dihydro-2H-1,3,4-oxadiazin-2-one

Product 1

HCID 666364695-(4-Chloro-phenyl)-3-(4-nitro-benzyl)-3,6-dihydro-[1,3,4]oxadiazin-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Step C (47.48 mmoles) in acetonitrile (260 ml) there are added 1-bromomethyl-4-nitro-benzene (52.23 mmoles) and potassium carbonate (189.92 mmoles). The reaction mixture is stirred at reflux for 4 hours under nitrogen. The reaction mixture is brought to ambient temperature and then diluted with 500 ml of DCM and 100 ml of water. Extraction with DCM (2×200 ml) is carried out and then the organic phases are combined. The organic phase obtained is washed with saturated NaCl solution and is then dried over sodium sulphate, filtered and concentrated to about 75 ml. After formation of a precipitate in suspension, ethyl ether (150 ml) is added, and stirred is carried out overnight at ambient temperature. The precipitate is filtered off, washed with ethyl ether and dried in vacuo to yield the title product, which is used directly in the next Step.

Workup

  1. temperatureat reflux for 4 hours under nitrogen
  2. customis brought to ambient temperature
  3. extractionExtraction with DCM (2×200 ml)
  4. customThe organic phase obtained
  5. washis washed with saturated NaCl solution
  6. dry with materialis then dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to about 75 ml
  9. additionAfter formation of a precipitate in suspension, ethyl ether (150 ml) is added
  10. stirringstirred
  11. filtrationThe precipitate is filtered off
  12. washwashed with ethyl ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-d010e7235791434fb2496fdcb1752bb4
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541412B2

Reaction notes

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