Dimethylformamide → HCID 13798269, compound

HRID 580263Notes

Reaction equation

HRID 580263 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[N:11]1.[CH:18](Br)([CH3:20])[CH3:19].[OH-].[Na+].CN(C)C=O>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:18]([CH3:20])[CH3:19])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[N:11]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 20134635HCID 20134635, compound

Product 1

HCID 13798269HCID 13798269, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(2,4-dichloro-5-hydroxyphenyl)-3,4,5-trimethylpyrazole (27.1 g), isopropyl bromide (12.3 g), aqueous sodium hydroxide (4.2 g) and dimethylformamide (150 ml) was stirred at 70° C. for 2 hours. To the reaction mixture, after cooling, were added water and toluene, to form two layers. The toluene layer as separated was washed with water and then dried over anhydrous sodium sulfate. Removal of the toluene by distillation in vacuo gave the titled compound (27.9 g) as a pale yellow oil, which was then purified through silica gel column chromatography to afford a white crystalline solid. m.p. 56°-58° C.

Workup

  1. temperatureTo the reaction mixture, after cooling
  2. customto form two layers
  3. customThe toluene layer as separated
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the toluene
  7. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-5943991ce70b439da617c6b71367d434
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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