Acetone → HCID 20430573, compound

HRID 2413179Notes

Reaction equation

HRID 2413179 reaction equation
[OH-:1].[Na+].S(O)(O)(=O)=O.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][NH:15][C:16]([NH2:18])=[NH:17].S([O-])([O-])(=O)=[O:20].[Na+].[Na+].[C:26](Cl)(=[O:29])[CH2:27][CH3:28].C[C:32](C)=[O:33]>>[C:26]([OH:29])(=[O:20])[CH2:27][CH2:28][C:32]([OH:33])=[O:1].[C:26]([N:15]([CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=1)[C:16]([NH2:18])=[NH:17])(=[O:29])[CH2:27][CH3:28]

Participants

6

Reactant 5

HCID 180Acetone2×HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 62324Propionyl chlorideHCID 178512760HCID 178512760, compound

Product 1

HCID 20430573HCID 20430573, compound

Procedure

A suspension of 8.00 g of 50% aqueous NaOH, 19.92 g of 2-pyridylmethyl guanidine sulfate and 100 ml of acetone is stirred for 31/2 hrs. at RT. 8 g of anhydrous sodium sulfate is added to the suspension and the reaction mixture stirred for 2 hrs. The reaction mixture is treated dropwise with a solution of 4.35 ml propionyl chloride in 100 ml acetone, stirred overnight at RT and filtered. The filtrate is evaporated in vacuo to a tan oil. The oil is dissolved in 100 ml of methylene chloride and the resulting solution is washed with H2O. The aqueous layer is extracted with methylene chloride. The combined organic extract is dried over sodium sulfate, filtered and evaporated in vacuo (0.1 mm) to an oil. The residue is dissolved in hot 2-propanol, 3.32 g succinic acid added, and the resulting mixture heated until a solid begins to form. The solid is collected, washed with 2-propanol and dried in vacuo to yield the desired guanidine succinate as a white powder, M.P. 168°-170° C.

Workup

  1. customat RT
  2. stirringthe reaction mixture stirred for 2 hrs
  3. stirringstirred overnight at RT
  4. filtrationfiltered
  5. customThe filtrate is evaporated in vacuo to a tan oil
  6. dissolutionThe oil is dissolved in 100 ml of methylene chloride
  7. washthe resulting solution is washed with H2O
  8. extractionThe aqueous layer is extracted with methylene chloride
  9. extractionThe combined organic extract
  10. dry with materialis dried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated in vacuo (0.1 mm) to an oil
  13. dissolutionThe residue is dissolved in hot 2-propanol
  14. addition3.32 g succinic acid added
  15. temperaturethe resulting mixture heated until a solid
  16. customto form
  17. customThe solid is collected
  18. washwashed with 2-propanol
  19. customdried in vacuo

Sources & evidence

ORD record
ord-ec9fcb03eb1d43579ae399a0c3a6d8a6
Source dataset
uspto-grants-1985_01
Patent number
US04496573

Reaction notes

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