Acetone → HCID 12922310, compound

HRID 436607Notes

Reaction equation

HRID 436607 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:5][N:6]([CH3:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:21]1(C)C=CC=CC=1.CC(C)=O.[S:32]([O:37]C)([O:35][CH3:36])(=[O:34])=[O:33]>>[CH3:36][O:35][S:32]([O-:37])(=[O:34])=[O:33].[CH3:1][O:2][C:3]1[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N+:5]([CH3:21])[N:6]([CH3:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 1140TolueneHCID 6497Dimethyl SulfateHCID 124985224-Methoxy-1-methyl-3,5-diphenyl-1H-pyrazole

Product 1

HCID 12922310HCID 12922310, compound

Conditions

Temperature
130 °C

Procedure

4-Methoxy-1-methyl-3,5-diphenylpyrazole (20 g, 0.076 mole) is suspended in dimethyl sulfate (23 g) at 20° C and the mixture is stirred and the reaction temperature raised to 130° C. At 70° C the mixture becomes a homogeneous solution and at 130° C some darkening occurs. After maintaining the reaction at 130° C for 1 hour, it is cooled and the mixture poured into toluene (250 ml). The toluene layer is decanted off and further toluene is added, decanted off, and this sequence repeated a third time. The residual oil, obtained from the above treatment, is then treated with acetone (10 ml) which has been dried over anhydrous potassium carbonate. This yields a crystalline product which is filtered off and washed with ether. The acetone filtrate is evaporated to give 27.5 g of oil, dissolved in water, and extracted with chloroform. The chloroform layer is evaporated to a small volume and then ether added. A white precipitate is obtained; combined yield 22 g (74%) of melting point 104.5°-105° C is obtained.

Workup

  1. customAt 70° C
  2. customat 130° C
  3. temperatureAfter maintaining
  4. customthe reaction at 130° C for 1 hour
  5. temperatureit is cooled
  6. customThe toluene layer is decanted off
  7. additionfurther toluene is added
  8. customdecanted off
  9. customThe residual oil, obtained from the above treatment
  10. dry with materialhas been dried over anhydrous potassium carbonate
  11. customThis yields a crystalline product which
  12. filtrationis filtered off
  13. washwashed with ether
  14. customThe acetone filtrate is evaporated

Sources & evidence

ORD record
ord-fb97276136054b40a486c8a15c3bd6e0
Source dataset
uspto-grants-1977_02
Patent number
US04009277

Reaction notes

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