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Hydrochloric Acid → 1-(4-methanesulfonyl-phenyl)-1H-pyrazole

HRID 2060080
Notes
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Reaction equation

HRID 2060080 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CO[CH:15](OC)[CH2:16][CH:17](OC)OC.Cl>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:17]=[CH:16][CH:15]=[N:12]2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66019TetramethoxypropaneHCID 701424-(Methylsulphonyl)phenylhydrazine

Product 1

HCID 214780151-(4-methanesulfonyl-phenyl)-1H-pyrazoleYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
0 °C

Procedure

To a solution of 4-(methylsulfonyl)phenylhydrazine (5.0 g, 26.8 mmol, 1.00 equiv) and 1,1,3,3-tetramethoxypropane (4.4 mL, 26.8, 1.0 equiv) in ethanol (37 mL) at rt was added concentrated HCl (2.8 mL). The resulting solution was heated at reflux for 1 hr, cooled to 0° C. and filtered to give 1-(4-methanesulfonyl-phenyl)-1H-pyrazole as a yellow solid (4.73 g, 79%). LCMS: (MH)+=223.1 (1.19 min).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 1 hr
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cf5f16db644e423890a415b90ce6cc83
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08278337B2

Reaction notes

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