P-Toluenesulfonylhydrazide → HCID 178424693, compound

HRID 1828198Notes

Reaction equation

HRID 1828198 reaction equation
[C:1]([C:4]([C:13]1[CH:24]=[CH:23][C:16]2[N:17]([CH3:22])[C:18](=[O:21])[N:19]([CH3:20])[C:15]=2[CH:14]=1)=[CH:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)(=O)[CH3:2].C1(C)C=CC(S([NH:34][NH2:35])(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:22][N:17]1[C:16]2[CH:23]=[CH:24][C:13]([C:4]3[C:1]([CH3:2])=[N:34][NH:35][C:5]=3[C:6]3[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=3)=[CH:14][C:15]=2[N:19]([CH3:20])[C:18]1=[O:21]

Participants

5

Reactant 3

HCID 15303P-Toluenesulfonylhydrazide2×HCID 516892Sodium BicarbonateHCID 69585563HCID 69585563, compound

Product 1

HCID 178424693HCID 178424693, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

5-(1-Acetyl-2-m-tolyl-vinyl)-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (1.07 g) in acetic acid (5 mL) was treated with p-toluenesulfonhydrazide (0.685 g). The reaction mixture was heated to 115° C. for 5 hours. Additional p-toluenesulfonhydrazide (0.601 g) was added and the reaction was heated for an additional 4 hours. The mixture was then allowed to cool, was poured onto saturated sodium bicarbonate and extracted into ethyl acetate. Chromatography on silica gel afforded 1,3-Dimethyl-5-(3-methyl-5-m-tolyl-1H-pyrazol-4-yl)-1,3-dihydro-benzoimidazol-2-one (0.263 g).

Workup

  1. temperaturethe reaction was heated for an additional 4 hours
  2. temperatureto cool
  3. extractionextracted into ethyl acetate

Sources & evidence

ORD record
ord-e30e24e018604a989a718bf354474c23
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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