Acetic Acid → HCID 178477344, compound

HRID 1825284Notes

Reaction equation

HRID 1825284 reaction equation
[I:1][C:2]1[C:10]2[C:9](=[S:11])[NH:8][CH:7]=[N:6][C:5]=2[NH:4][N:3]=1.[C:12](O)(=O)[CH3:13]>[OH-].[K+].O>[CH2:12]([S:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[NH:4][N:3]=[C:2]([I:1])[C:10]=12)[CH3:13]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178527907HCID 178527907, compound

Product 1

HCID 178477344HCID 178477344, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

Compound 5 (43.5 g, 157 mmol) was stirred in potassium hydroxide solution (38.6 g KOH in 350 mL of water) for 30 min. The mixture was filtered and the filtrate was acidified to pH 10 by addition of acetic acid and then diluted with 350 mL of absolute ethanol. Iodoethane (10 mL) was added and the solution was stirred at room temperature. Additional 10 mL aliquots of iodoethane were added after 30 min. and 1.0 h. The reaction was complete after a total of 90 min. Other runs required further addition of iodoethane to complete the reaction. The reaction solution was diluted with 700 mL of water and 20 mL of acetic acid. The mixture was cooled in an ice-bath and the solid was filtered, rinsed with water and dried. This crude product was dissolved in 300 of DMF and stirred at 90° C. for 15 min. Insoluble material was filtered away and the filtrate was diluted with 1 L of water and cooled in an ice-water bath. The solid was filtered, rinsed with water and dried: 19 g (40%) yield.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was acidified to pH 10 by addition of acetic acid
  3. additiondiluted with 350 mL of absolute ethanol
  4. additionIodoethane (10 mL) was added
  5. additionAdditional 10 mL aliquots of iodoethane were added after 30 min. and 1.0 h
  6. customafter a total of 90 min
  7. additionfurther addition of iodoethane
  8. customthe reaction
  9. temperatureThe mixture was cooled in an ice-bath
  10. filtrationthe solid was filtered
  11. washrinsed with water
  12. customdried
  13. dissolutionThis crude product was dissolved in 300 of DMF
  14. stirringstirred at 90° C. for 15 min
  15. filtrationInsoluble material was filtered away
  16. additionthe filtrate was diluted with 1 L of water
  17. temperaturecooled in an ice-water bath
  18. filtrationThe solid was filtered
  19. washrinsed with water
  20. customdried
  21. custom19 g (40%) yield

Sources & evidence

ORD record
ord-b52ee88919e146f89f5b20d44fa13c24
Source dataset
uspto-grants-2006_05
Patent number
US07045610B2

Reaction notes

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