Pyridine → 2-(4-Fluorophenyl)-5-[-1-(methoxyimino)ethyl]-3-[4-(methylsulfonyl)phenyl]thiophene

HRID 1899087Notes

Reaction equation

HRID 1899087 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:5]=1)(=O)[CH3:2].Cl.[CH3:27][O:28][NH2:29].N1C=CC=CC=1>O1CCOCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[S:8][C:4]([C:1](=[N:29][O:28][CH3:27])[CH3:2])=[CH:5][C:6]=2[C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 106431405-Acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene

Product 1

HCID 539439192-(4-Fluorophenyl)-5-[-1-(methoxyimino)ethyl]-3-[4-(methylsulfonyl)phenyl]thiopheneYield 46.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (1.35 g), methoxyamine hydrochloride (0.45 g) and pyridine (0.44 ml) in dioxane (17 ml) was stirred at ambient temperature for 1 hour. The mixture was concentrated, and the residue was triturated with water, filtered, washed with water and dried. The crude crystals were recrystallized from ethyl acetate to give pure crystals of 2-(4-fluorophenyl)-5-[-1-(methoxyimino)ethyl]-3-[4-(methylsulfonyl)phenyl]thiophene (0.68 g).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-77887b6dfd484558859655e46a0f65da
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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