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

HRID 2102315
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576063B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes