Potassium Carbonate → 4H-1,3,4-Oxadiazin-5(6H)-one, 2-(2,6-dimethylimidazo(1,2-a)pyridin-3-yl)-

HRID 986386Notes

Reaction equation

HRID 986386 reaction equation
Cl[CH2:2][C:3]([NH:5][NH:6][C:7]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[CH3:19])=[O:8])=[O:4].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C.CN(C)C=O>[CH3:19][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]2[C:9]=1[C:7]1[O:8][CH2:2][C:3](=[O:4])[NH:5][N:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 14032941HCID 14032941, compound

Product 1

HCID 30653094H-1,3,4-Oxadiazin-5(6H)-one, 2-(2,6-dimethylimidazo(1,2-a)pyridin-3-yl)-Yield 16.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 21 g of N'-chloroacetyl-2,6-dimethylimidazo[1,2-a]pyridine-3-carbohydrazide and 30 g of potassium carbonate in 200 ml of methyl ethyl ketone and 100 ml of dimethylformamide is stirred with refluxing for 5 hours. After insoluble substances are filtered off, the solvent is distilled off and water is added to the resultant residue. The precipitated crystals are collected by filtration and recrystallized from methanol to give 3 g of 2-(2,6-dimethylimidazo[1,2-a]pyridin-3-yl)-4,6-dihydro-1,3,4-oxadiazin-5-one as white crystals, melting at 313° C. with decomposition.

Workup

  1. temperaturewith refluxing for 5 hours
  2. filtrationAfter insoluble substances are filtered off
  3. distillationthe solvent is distilled off
  4. additionwater is added to the resultant residue
  5. filtrationThe precipitated crystals are collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c3f4f0b9ac544bca8fd260158c94a46c
Source dataset
uspto-grants-1987_12
Patent number
US04713381

Reaction notes

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