Dimethylformamide → (2E)-3-(dimethylamino)-1-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]prop-2-en-1-one

HRID 45874Notes

Reaction equation

HRID 45874 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=3)=[N:9]2)=[CH:5][CH:4]=1.[CH3:27][N:28]([CH3:31])[CH:29]=O>O1CCCC1>[CH3:27][N:28]([CH3:31])/[CH:29]=[CH:14]/[C:13]([C:11]1[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[N:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:26][CH:25]=2)[CH:12]=1)=[O:15]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 67185282HCID 67185282, compound

Product 1

HCID 67186714(2E)-3-(dimethylamino)-1-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]prop-2-en-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

460 mg (1.3 mmol) of 1-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-ethanone were dissolved in 25 ml of dry tetrahydrofuran and 15 ml of dimethylformamide di-tert-butylacetale (62 mmol) were added to the resulting solution. The reaction was heated at 70° C. under stirring for 6 hours. The solvent was then evaporated in vacuo and the residue diluted with dichloromethane and washed with water. The organic layer was finally dried over sodium sulphate and evaporated, giving 500 mg (96%) of the title compound as an oil.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionthe residue diluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was finally dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-cc49df4559dd43c8ac300273b1a9dc97
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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