Sulfuric Acid → HCID 178474535, compound

HRID 1059889Notes

Reaction equation

HRID 1059889 reaction equation
O[CH:2]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1)[C:3]1[S:7][C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[N:5][C:4]=1[CH3:12].S(=O)(=O)(O)O.[OH-:25].[Na+].[C:27](#[N:29])[CH3:28]>>[C:27]([NH:29][CH:2]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1)[C:3]1[S:7][C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[N:5][C:4]=1[CH3:12])(=[O:25])[CH3:28]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 178428529HCID 178428529, compound

Product 1

HCID 178474535HCID 178474535, compound

Procedure

A solution of N-(5-(hydroxy-(4-methylpyridin-2-yl)methyl)-4-methylthiazol-2-yl)guanidine (0.54 g) and 96% sulfuric acid (6.5 ml) in acetonitrile (26 ml) was stirred at 5° C. for 18 hours. The pH of the mixture was adjusted to 12 with 4N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate three times. The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with ethyl acetate, collected by filtration and dried. The crude compound was recrystallized from ethanol/n-hexane to give N-(5-(acetylamino-(4-methylpyridin-2-yl)methyl)-4-methylthiazol-2-yl)-guanidine (211 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with ethyl acetate
  6. filtrationcollected by filtration
  7. customdried
  8. customThe crude compound was recrystallized from ethanol/n-hexane

Sources & evidence

ORD record
ord-8f4da7a7e4744621b67a1e0d4d35df92
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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