Sodium Hydroxide → HCID 178512550, compound

HRID 2413143Notes

Reaction equation

HRID 2413143 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].C([N:13]=[C:14]([NH2:28])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[N:17]=1)(C)(C)C.[OH-:29].[Na+]>S(=O)(=O)(O)O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22][CH2:23][CH2:24][CH2:25][C:26]([NH2:27])=[O:29])[N:17]=1)[C:14]([NH2:28])=[NH:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70433060HCID 70433060, compound

Product 1

HCID 178512550HCID 178512550, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-[2-(2-t-butylguanidino)pyrid-6-ylthio]butyronitrile hydrogen maleate (0.1 g.) in concentrated sulphuric acid (0.5 ml.) was kept at room temperature for 72 hours. The solution was added to crushed ice and then basified with 10N aqueous NaOH and the mixture extracted three times with EtOAc. The combined extracts were dried and evaporated to dryness. A solution of the residue in acetone was added to a solution of maleic acid in acetone, and the crystalline precipitate was collected to give 4-(2-guanidinopyrid-6-ylthio)butyramide hydrogen maleate (0.04 g.), m.p. 169°-170°.

Workup

  1. additionThe solution was added
  2. customto crushed ice
  3. extractionthe mixture extracted three times with EtOAc
  4. customThe combined extracts were dried
  5. customevaporated to dryness
  6. additionA solution of the residue in acetone was added to a solution of maleic acid in acetone
  7. customthe crystalline precipitate was collected

Sources & evidence

ORD record
ord-c2ad337f1d9e4677a14b0e3096fda272
Source dataset
uspto-grants-1985_01
Patent number
US04496564

Reaction notes

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