Water → HCID 86602113, compound

HRID 2355788Notes

Reaction equation

HRID 2355788 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)([OH:5])[CH3:4].[OH-].[Na+].Cl[C:18]1[N:19]=[C:20]([NH2:23])[S:21][CH:22]=1.O>CCO>[NH2:23][C:20]1[S:21][CH:22]=[C:18]([S:12][C:9]2[CH:10]=[CH:11][C:6]([C:3]([OH:5])([CH3:4])[C:2]([F:1])([F:13])[F:14])=[CH:7][CH:8]=2)[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 98339722-Amino-4-chlorothiazoleHCID 59753102HCID 59753102, compound

Product 1

HCID 86602113HCID 86602113, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1,1,1-trifluoro-2-(4-mercaptophenyl)propan-2-ol (5.7 g, 25 mmol) was added NaOH (1.7 g, 42 mmol), a solution of 4-chlorothiazol-2-amine (2.5 g, 18 mmol) in EtOH (18 mL), and water (36 mL). The mixture was brought to reflux and stirred for 2 h. The solution was poured onto water (100 mL) and extracted with Et2O (3×50 mL). The combined organics were washed with brine (100 mL) and dried over MgSO4 and concentrated in vacuo to provide 3.65 g of 2-(4-(2-aminothiazol-4-ylthio)phenyl)-1,1,1-trifluoropropan-2-ol.

Workup

  1. temperatureto reflux
  2. additionThe solution was poured onto water (100 mL)
  3. extractionextracted with Et2O (3×50 mL)
  4. washThe combined organics were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b99726f1df847faa5dd8bfe91f95825
Source dataset
uspto-grants-2010_07
Patent number
US07754890B2

Reaction notes

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