Water → 3-(Benzyloxy)-5-(4-methoxyphenyl)-1-(propan-2-yl)-1H-pyrazole

HRID 2102315Notes

Reaction equation

HRID 2102315 reaction equation
[CH2:1]([O:8][C:9](=S)[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH:23]([NH:26][NH2:27])([CH3:25])[CH3:24].C(N(CC)CC)C.O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:26]([CH:23]([CH3:25])[CH3:24])[N:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 15439079HCID 15439079, compound

Product 1

HCID 230795283-(Benzyloxy)-5-(4-methoxyphenyl)-1-(propan-2-yl)-1H-pyrazoleYield 62.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-(4-methoxyphenyl)-3-oxothiopropionic acid O-benzyl ester (0.60 g) and isopropylhydrazine hydrochloride (0.29 g) in acetonitrile (2 mL) was added triethylamine (0.81 g) and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and the mixture was extracted with dichloromethane. The solvent of the organic layer was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=3/1-1/3) to give the title compound (0.40 g).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe solvent of the organic layer was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=3/1-1/3)

Sources & evidence

ORD record
ord-55b1d1401ee94798a48116c46a21bc04
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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