4-(Methylsulfonyl)phenylhydrazine hydrochloride → HCID 10868699, compound

HRID 2060084Notes

Reaction equation

HRID 2060084 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CN(C)[CH:16]=[CH:17][C:18](=O)[CH:19](OC)[O:20]C>C(O)C>[CH3:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:18]([CH:19]=[O:20])=[CH:17][CH:16]=[N:13]2)=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 27351814-(Methylsulfonyl)phenylhydrazine hydrochlorideHCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one

Product 1

HCID 10868699HCID 10868699, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-(methylsulfonyl)phenylhydrazine hydrochloride (0.75 g, 4.02 mmol, 1.00 equiv) in ethanol (20 mL) was added 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (0.7 g, 4.0 mmol, 1.0 equiv). The resulting mixture was heated at reflux (48 hr) then concentrated. To a solution of the crude residue in acetone (10 mL) was added 6N HCl (2 mL). The resulting solution was allowed to stir at room temperature for 30 min, then was partitioned between ethyl acetate and water. The organic extract was washed with water, saturated sodium bicarbonate, brine and dried (sodium sulfate). Concentration afforded 2-(4-methanesulfonyl-phenyl)-2H-pyrazole-3-carbaldehyde admixed with regioisomer 1-(4-methanesulfonyl-phenyl)-1H-pyrazole-3-carbaldehyde (ca. 10/1). The crude material was used without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux (48 hr)
  3. concentrationthen concentrated
  4. additionTo a solution of the crude residue in acetone (10 mL) was added 6N HCl (2 mL)
  5. customwas partitioned between ethyl acetate and water
  6. extractionThe organic extract
  7. washwas washed with water, saturated sodium bicarbonate, brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationConcentration

Sources & evidence

ORD record
ord-a791f93b000849a281227383eebecf77
Source dataset
uspto-grants-2012_10
Patent number
US08278337B2

Reaction notes

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