Potassium Carbonate → 4H-1,3,4-Oxadiazin-5(6H)-one, 2-(2,8-dimethylimidazo(1,2-a)pyridin-3-yl)-

HRID 986385Notes

Reaction equation

HRID 986385 reaction equation
Cl[CH2:2][C:3]([NH:5][NH:6][C:7]([C:9]1[N:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]2=[N:11][C:10]=1[CH3:19])=[O:8])=[O:4].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:19][C:10]1[N:11]=[C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[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

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20157428HCID 20157428, compound

Product 1

HCID 30653084H-1,3,4-Oxadiazin-5(6H)-one, 2-(2,8-dimethylimidazo(1,2-a)pyridin-3-yl)-Yield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 g of N'-chloroacetyl-2,8-dimethylimidazo[1,2-a]pyridine-3-carbohydrazide and 10 g of potassium carbonate in 50 ml of dimethylformamide is stirred under heating at 70°-90° C. for 1.5 hours. After the reaction mixture is allowed to cool, insoluble substances are collected by filtration, washed with water and recrystallized from a mixted solvent of chloroform and methanol to give 2.0 g of 2-(2,8-dimethylimidazo[1,2-a]pyridin-3-yl)-4,6-dihydro-1,3,4-oxadiazin-5-one as white crystals, melting at 310°-313° C. with decomposition.

Workup

  1. temperatureunder heating at 70°-90° C. for 1.5 hours
  2. temperatureto cool
  3. filtrationinsoluble substances are collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixted solvent of chloroform and methanol

Sources & evidence

ORD record
ord-f0d6941098564c7297eb4528ba00a0ee
Source dataset
uspto-grants-1987_12
Patent number
US04713381

Reaction notes

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