Phenylhydrazine → HCID 15337398, compound

HRID 441159Notes

Reaction equation

HRID 441159 reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=O)=[CH:12][CH:11]=1.CSC1C=CC(C=O)=CC=1.FC1C=CC(CCl)=CC=1>C1(C)C=CC=CC=1.CC(O)=O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:6]3[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=3)[NH:7][C:17]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 7516PhenylhydrazineHCID 96024-Fluorobenzyl chlorideHCID 769854-(Methylthio)benzaldehydeHCID 11197095HCID 11197095, compound

Product 1

HCID 15337398HCID 15337398, compound

Reagents, catalysts & solvents 1

HCID 18331056Acetic acid tolueneSolvent

Procedure

To phenylhydrazine (50 uL) in toluene-HOAc (2:1, 2 mL) was added 2-(4-fluorophenyl)-1-(4-(methylsulfonyl)phenyl)ethanone (105 mg) (prepared from 4-(methylthio)benzaldehyde and 4-fluorobenzyl chloride by the same method as described in Step 1 of Example 4). After 1 hr at 85° C., the reaction mixture was extracted with EtOAc and HCl. After drying over NaSO4 and evaporation in vacuo the title compound was purified by flash chromatography (67 mg).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc and HCl
  2. dry with materialAfter drying over NaSO4 and evaporation in vacuo the title compound
  3. customwas purified by flash chromatography (67 mg)

Sources & evidence

ORD record
ord-7a007ac9cdab40358cecf633ee5e1d0e
Source dataset
uspto-grants-1996_05
Patent number
US05521213

Reaction notes

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