Dimethylformamide → HCID 23157275, compound

HRID 2110867Notes

Reaction equation

HRID 2110867 reaction equation
[C:1]([C:5]1[CH2:6][C:7](=[O:10])[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].CN(C)[CH:31]=[O:32]>O>[C:1]([C:5]1[CH:6]=[C:7]([O:10][CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[N:8]([CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:23]([O:32][CH3:31])=[O:26])=[CH:15][CH:14]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 5204213-tert-Butyl-2-pyrazolin-5-one

Product 1

HCID 23157275HCID 23157275, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-tert-butyl-2,4-dihydro-3H-pyrazol-3-one (5.00 g, 35.7 mmol), methyl 4-(bromomethyl)benzoate (17.16 g, 74.91 mmol), potassium carbonate (10.5 g, 76.0 mmol) and N,N-dimethylformamide (50 mL) was stirred overnight at 60° C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (6.90 g, yield 44%) as a colorless oil. melting point 93-94° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract washed with aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8081945f9ee743c7bd1622db8e70da6c
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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