76700-85-1 → HCID 20202839, compound

HRID 544577Notes

Reaction equation

HRID 544577 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][NH:4][C:5]([NH:7][C:8]([NH2:10])=[S:9])=[NH:6].Cl[CH2:14][C:15](=O)[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>CCO>[F:12][C:2]([F:1])([F:11])[CH2:3][N:4]=[C:5]([NH2:6])[NH:7][C:8]1[S:9][CH:14]=[C:15]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[N:10]=1

Participants

4

Reactant 2

HCID 1111662576700-85-1HCID 178512206HCID 178512206, compound

Product 1

HCID 20202839HCID 20202839, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 2,2,2-trifluoroethylamidinothiourea (2.1 g.) in hot EtOH (20 ml.) was added a solution of methyl 6-chloro-5-oxohexanoate (2.0 g.) in hot EtOH (20 ml.). The mixture was heated under reflux for 1 hour and then evaporated to dryness. The residue was partitioned between ether (20 ml.) and water (60 ml.). The aqueous layer was separated, basified with sodium bicarbonate and extracted with EtOAc. The organic layer was evaporated to dryness to give a gum which was recrystallised from EtOAc/ether/acetone to give methyl 4-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]butyrate which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to dryness
  4. customThe residue was partitioned between ether (20 ml.) and water (60 ml.)
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc
  7. customThe organic layer was evaporated to dryness
  8. customto give a gum which
  9. customwas recrystallised from EtOAc/ether/acetone

Sources & evidence

ORD record
ord-b6e9ce6f7c9249bcac5b934657157ae6
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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