Pyridine → HCID 21525330, compound

HRID 1658693Notes

Reaction equation

HRID 1658693 reaction equation
[CH3:1][NH:2][CH2:3][NH:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[OH-].[Na+].[C:18](Cl)(Cl)=[O:19].N1C=CC=CC=1>O.COCCOC>[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([C:5]2[O:15][C:18](=[O:19])[N:2]([CH3:1])[CH2:3][N:4]=2)=[CH:11][CH:10]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 21525332HCID 21525332, compound

Product 1

HCID 21525330HCID 21525330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A suspension of 24.6 g (0.1 mole) of N-(methylaminomethyl)-4-nitro-benzamide in 300 ml of water is neutralised at 0°-25°C with 50 ml of 2 normal sodium hydroxide solution (0.1 mole). The neutralised product is filtered off and dried in vacuo. It is then taken up in 150 ml of 1,2-dimethoxyethane and this solution is treated at 0°-25°C over the course of 1 hour with 9.9 g (0.1 mole) of phosgene in 150 ml of 1,2-dimethoxyethane. A solution of 15.8 g (0.2 mole) of pyridine in 150 ml of 1,2-dimethoxyethane is then added over the course of a further hour. Stirring of the reaction mixture is continued for 2 hours and then it is refluxed for 5 hours. After the reaction mixture has cooled, the precipitate which has formed is collected by filtration, the residue is dissolved in methylene chloride and washed first with sodium bicarbonate solution and then with water and dried. The solvent is evaporated and the residue is recrystallised from ethyl acetate to yield 6-(4-nitro-phenyl)-3-methyl-3,4-dihydro-2H-1,3,5-oxadiazin-2-one with a melting point of 153°-154°C (compound 2).

Workup

  1. filtrationThe neutralised product is filtered off
  2. customdried in vacuo
  3. temperatureit is refluxed for 5 hours
  4. temperatureAfter the reaction mixture has cooled
  5. customthe precipitate which has formed
  6. filtrationis collected by filtration
  7. dissolutionthe residue is dissolved in methylene chloride
  8. washwashed first with sodium bicarbonate solution
  9. dry with materialwith water and dried
  10. customThe solvent is evaporated
  11. customthe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-9cdf207213d64613b406dee771a1dcf5
Source dataset
uspto-grants-1976_06
Patent number
US03966721

Reaction notes

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