Phenylhydrazine → HCID 15337398, compound

HRID 2269574Notes

Reaction equation

HRID 2269574 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 111970952-(4-Fluorophenyl)-1-(4-(methylsulfonyl)phenyl)ethanone

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-e8ffa0a5a5fb4221afba28f19d347cd2
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

Loading…