Methyl iodide → HCID 22031037, compound

HRID 1792465Notes

Reaction equation

HRID 1792465 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([NH:13][NH2:14])=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[OH-].[Na+].[CH3:17]I.C(=O)([O-])[O-].[K+].[K+].[C:25](=[S:27])=S>O.C(OCC)(=O)C.CN(C)C=O.C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[O:12][C:17]([S:27][CH3:25])=[N:14][N:13]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

10

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 23537414HCID 23537414, compound

Product 1

HCID 22031037HCID 22031037, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 276), 0.24 mL carbon disulfide, 157 mg sodium hydroxide, 15 mL ethanol and 15 mL water was heated for 5 hours under reflux. The reaction solution was poured into a mixture of iced water and an aqueous saturated ammonium chloride solution, and the precipitated crystals were collected by filtration. 1 N hydrochloric acid was added to the filtrate, and the resulting crystals were also collected by filtration. The combined crystals were dried under reduced pressure by a vacuum pump, to give 1.12 g crude product of 5-(6-bromoimidazo[1,2-a]pyridin-3-yl)[1,3,4)oxadiazole-2-thiol as pale brown crystals. 60 μL methyl iodide was added to a mixture of 258 mg of this thiol derivative, 242 mg potassium carbonate and 30 mL N,N-dimethylformamide under ice-coolingd water in a stream of nitrogen, and the mixture was stirred for 10 minutes. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The aqueous layer was saturated with common salt and then extracted with ethyl acetate. The combined organic layer was washed twice with water and then with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. Hexane was added to the resulting residues, the crystals were collected by filtration and dried under reduced pressure with a vacuum pump. 245 mg of the title compound was obtained as pale brown crystals.

Workup

  1. temperaturewas heated for 5 hours
  2. temperatureunder reflux
  3. filtrationan aqueous saturated ammonium chloride solution, and the precipitated crystals were collected by filtration
  4. addition1 N hydrochloric acid was added to the filtrate
  5. filtrationthe resulting crystals were also collected by filtration
  6. customThe combined crystals were dried under reduced pressure by a vacuum pump
  7. customto give 1.12 g crude product of 5-(6-bromoimidazo[1,2-a]pyridin-3-yl)[1,3,4)oxadiazole-2-thiol as pale brown crystals
  8. customthe organic layer was separated
  9. extractionextracted with ethyl acetate
  10. washThe combined organic layer was washed twice with water
  11. dry with materialwith brine and dried over anhydrous sodium sulfate
  12. filtrationThe drying agent was filtered off
  13. customthe filtrate was evaporated
  14. additionHexane was added to the resulting residues
  15. filtrationthe crystals were collected by filtration
  16. customdried under reduced pressure with a vacuum pump

Sources & evidence

ORD record
ord-d82e24a2be0747a08b3ebbc045c400ba
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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