Sodium hydride → 5-(4-Chlorophenyl)-3,6-dihydro-2H-1,3,4-oxadiazin-2-one

HRID 44288Notes

Reaction equation

HRID 44288 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[N:13][NH:14][C:15]([O:17][CH2:18]C)=[O:16])CO)=[CH:6][CH:5]=1>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:18][O:17][C:15](=[O:16])[NH:14][N:13]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86662431Ethyl N'-[1-(4-chloro-phenyl)-2-hydroxy-ethylidene]-hydrazinecarboxylate

Product 1

HCID 133659155-(4-Chlorophenyl)-3,6-dihydro-2H-1,3,4-oxadiazin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in oil, 16 mmoles) is added, in small portions and at ambient temperature, to a solution of the compound obtained in Step B (100.5 mmoles) in ethanol (800 ml). After reacting for 2 hours, the reaction mixture is cooled to 0° C. and stirring is continued for 30 minutes. The precipitate formed is filtered off, washed with cold ethanol and then dried in vacuo to yield the title product, which is used directly in the next Step.

Workup

  1. waitis continued for 30 minutes
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with cold ethanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e5063e62024345d4b15821f023311991
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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