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

HRID 1365025
Notes
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Reaction equation

HRID 1365025 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-oxothio-propionic 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-71e51ce1462d449a9a1b6269510bb3ac
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888487B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes