Water → HCID 178513008, compound

HRID 247584Notes

Reaction equation

HRID 247584 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)(=[O:7])=[O:6].O.S(O)(O)(=O)=O.CS[C:26](=[NH:28])[NH2:27].[OH-].[Na+]>CO>[NH:1]([CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)(=[O:7])=[O:6])[C:26]([NH2:28])=[NH:27]

Participants

6

Reactant 4

HCID 962WaterHCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 178513008HCID 178513008, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 ml of methanol was dissolved 3.3 g of N-(2-aminoethyl)-5-isoquinolinesulfonamide obtained in Referential example 1, and to the solution was added 25 ml of water solution containing 5.0 g of S-methylisothiourea sulfate. And to the mixed solution was added 1N aqueous sodium hydroxide solution, the mixed solution thus obtained was heated at reflux for two hours. After the reflux, the methanol was distilled therefrom under reduced pressure, and the white crystals precipitated were separated by filtration under reduced pressure. The crystalline residue thus obtained was recrystallized from methanol to give 3.24 g of N-(2-guanidinoethyl)-5-isoquinolinesulfonamide, i.e., Compound (2) in a yield of 84%.

Workup

  1. customobtained in Referential example 1
  2. customthe mixed solution thus obtained
  3. temperaturewas heated
  4. temperatureat reflux for two hours
  5. distillationAfter the reflux, the methanol was distilled
  6. customunder reduced pressure, and the white crystals precipitated
  7. customwere separated by filtration under reduced pressure
  8. customThe crystalline residue thus obtained
  9. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-a3d115384dbb41d79a84fc75fcc3c33c
Source dataset
uspto-grants-1987_11
Patent number
US04709032

Reaction notes

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