Water → HCID 66820792, compound

HRID 386382Notes

Reaction equation

HRID 386382 reaction equation
[C:1]1([N:11]2[C:15]([SH:16])=[CH:14][CH:13]=[N:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:24][C:18]([S:16][C:15]1[N:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:12]=[CH:13][CH:14]=1)([CH3:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178527733HCID 178527733, compound

Product 1

HCID 66820792HCID 66820792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(naphthalen-1-yl)-1H-pyrazole-5-thiol (120 mg, 0.53 mmol), ethyl bromoisobutyrate (0.09 mL, 0.58 mmol) and potassium carbonate (81 mg, 0.58 mmol) in DMF (3 mL) was stirred at room temperature for 16 hours. Water was then added to the reaction mixture, extracted with ethyl acetate, dried over sodium sulfate and concentrated. Purification by preparative thin layer chromatography (95% dichloromethane/5% acetone) afforded ethyl 2-methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-ylthio)propanoate as a solid. (124 mg, 69%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by preparative thin layer chromatography (95% dichloromethane/5% acetone)

Sources & evidence

ORD record
ord-9f8b60f46ff3455d86734deff7a6dfc6
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

Loading…