Potassium Carbonate → HCID 789488, compound

HRID 614336Notes

Reaction equation

HRID 614336 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C)C=O>[C:12]1([N:11]2[C:2]3=[N:3][CH:4]=[CH:5][CH:6]=[C:7]3[NH:8][C:9]2=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 2800781Urea, N-(2-chloro-3-pyridinyl)-N'-phenyl-

Product 1

HCID 789488HCID 789488, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.7 g. (0.023 mole) of the product from Step A, 3.45 g. (0.025 mole) of potassium carbonate, 20 mg. of copper powder and 50 ml. of dimethyl formamide was refluxed for 21/2 hours. The cooled mixture was filtered and the solvent was evaporated in vacuo. The oily residue was extracted with 100 ml. of 1 N. sodium hydroxide solution and the extract was treated with decolorizing charcoal and filtered. The filtrate was neutralized with acetic acid. The crystalline precipitate of 600 mg. of 3-phenyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, m.p. 233°-235° C. was collected.

Workup

  1. additionA mixture of 5.7 g
  2. filtrationThe cooled mixture was filtered
  3. customthe solvent was evaporated in vacuo
  4. extractionThe oily residue was extracted with 100 ml
  5. additionsodium hydroxide solution and the extract was treated with decolorizing charcoal
  6. filtrationfiltered
  7. customof 3-phenyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, m.p. 233°-235° C. was collected

Sources & evidence

ORD record
ord-a81ac58e034543c28642d9d8a23bb500
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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