Water → HCID 178512681, compound

HRID 1980716Notes

Reaction equation

HRID 1980716 reaction equation
Cl.[NH:2]([C:6]1[S:7][C:8]([C:11](OCC)=[O:12])=[CH:9][N:10]=1)[C:3]([NH2:5])=[NH:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:2]([C:6]1[S:7][C:8]([CH2:11][OH:12])=[CH:9][N:10]=1)[C:3]([NH2:5])=[NH:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178469834HCID 178469834, compound

Product 1

HCID 178512681HCID 178512681, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-guanidino-5-thiazolecarboxylate hydrochloride (1.0 g; 3.99 mmoles) [prepared in Step A] was added to a cooled (ice-water bath) suspension of lithium aluminum hydride (0.46 g; 12.1 mmoles) in 25 ml of tetrahydrofuran. The reaction mixture was then heated at reflux temperature for 2 hours, cooled, decomposed with 0.46 ml H2O, 0.46 ml of 15% NaOH and 1.38 ml H2O and filtered. The filtrate was dried and evaporated under reduced pressure to give 0.61 g of product. Recrystallization from acetonitrile yielded the title compound, mp 168°-170°.

Workup

  1. temperaturea cooled
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux temperature for 2 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe filtrate was dried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dac6edefc66f4f56b78786ba9ad03df1
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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