HCID 21298739, compound → 2-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazole

HRID 34761Notes

Reaction equation

HRID 34761 reaction equation
ClCC(=O)CCCC[N:8]1[C:12](=O)[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=C2C1=O.[F:20][C:21]([F:31])([F:30])[CH2:22][NH:23][C:24]([NH:26][C:27]([NH2:29])=[S:28])=[NH:25]>C(O)C>[F:31][C:21]([F:20])([F:30])[CH2:22][N:23]=[C:24]([NH2:25])[NH:26][C:27]1[S:28][CH:17]=[C:16]([CH2:15][CH2:14][CH2:11][CH2:12][NH2:8])[N:29]=1

Participants

4

Reactant 2

HCID 21298739HCID 21298739, compoundHCID 178512206HCID 178512206, compound

Product 1

HCID 212987102-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of N-(6-chloro-5-oxohexyl)phthalimide (3.4 g.) in ethanol was added N-(2,2,2-trifluoroethylamidino)thiourea (2.75 g.) in ethanol (30 ml.). The mixture was heated under reflux for 2 hours and the reaction mixture concentrated to small volume by evaporation. Following treatment of the resulting solution with ether until the solution was just turbid, crystalline 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-phthalimidobutyl)thiazole hydrochloride (3.6 g.) was precipitated. This material (2.1 g.) in ethanol (20 ml.) and water (5 ml.) was heated to boiling and the solution pH was adjusted to 12 by addition of 2N sodium hydroxide. After heating on a steam bath for 10 minutes, the solution pH was adjusted to 3 with conc. hydrochloric acid and heating continued for a further 0.5 hour. The solution was cooled, adjusted to pH 12 with 2N sodium hydroxide and extracted with ethyl acetate (2×30 ml.). Evaporation of the washed (H2O), dried (magnesium sulphate) extract gave 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole as a pale yellow gum which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationthe reaction mixture concentrated to small volume by evaporation
  4. customwas precipitated
  5. temperatureThis material (2.1 g.) in ethanol (20 ml.) and water (5 ml.) was heated
  6. additionthe solution pH was adjusted to 12 by addition of 2N sodium hydroxide
  7. temperatureAfter heating on a steam bath for 10 minutes
  8. temperatureheating
  9. temperatureThe solution was cooled
  10. extractionextracted with ethyl acetate (2×30 ml.)
  11. customEvaporation of the
  12. washwashed (H2O)
  13. dry with materialdried (magnesium sulphate)
  14. extractionextract

Sources & evidence

ORD record
ord-a7b8b142b85747d7a0901b95a8269b86
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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