Water → HCID 20202856, compound

HRID 543779Notes

Reaction equation

HRID 543779 reaction equation
Cl.[F:2][C:3]([F:17])([F:16])[CH2:4][N:5]=[C:6]([NH2:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13]Cl)[N:12]=1.[OH-].[Na+].O.[SH:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]>CCO>[F:2][C:3]([F:17])([F:16])[CH2:4][N:5]=[C:6]([NH2:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][S:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18050Methyl 3-mercaptopropionateHCID 86739395HCID 86739395, compound

Product 1

HCID 20202856HCID 20202856, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[2,2,2-trifluoroethyl]guanidino-4-chloromethylthiazole hydrochloride (4.6 g.) in EtOH (75 ml.) and methyl 3-mercaptopropionate (2.47 ml.) at 5° was treated dropwise with aqueous sodium hydroxide (1.8 g. in 15 ml. of water) over 10 minutes. The resulting solution was allowed to reach room temperature and was stirred for 1 hour. It was then poured into water and the precipitate filtered and crystallised from EtOH to give methyl 3-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-ylmethylthio]propionate (1.93 g), m.p. 96°-98°.

Workup

  1. customto reach room temperature
  2. filtrationthe precipitate filtered
  3. customcrystallised from EtOH

Sources & evidence

ORD record
ord-850dd28f0f684dc69956695fc05cd91b
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

Loading…