Pyridine → 2'-(2,4-Difluorophenylthio)-4'-[1-(methoxyimino)ethyl]methanesulfonanilide

HRID 1087214Notes

Reaction equation

HRID 1087214 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([S:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:5]=1)(=O)[CH3:2].Cl.[O:25]([NH2:27])[CH3:26].N1C=CC=CC=1>C(O)C>[F:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[S:15][C:6]1[CH:5]=[C:4]([C:1](=[N:27][O:25][CH3:26])[CH3:2])[CH:14]=[CH:13][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10450972Methanesulfonamide, N-[4-acetyl-2-[(2,4-difluorophenyl)thio]phenyl]-

Product 1

HCID 544542462'-(2,4-Difluorophenylthio)-4'-[1-(methoxyimino)ethyl]methanesulfonanilideYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide (0.9 g), methoxylamine hydrochloride (0.21 g) and pyridine (0.2 g) in ethanol (15 ml) was refluxed for 4 hours. The mixture was concentrated under reduced pressure, and the residue was triturated with water to give a powder. The powder was recrystallized from ethanol to give 2'-(2,4-difluorophenylthio)-4'-[1-(methoxyimino)ethyl]methanesulfonanilide (0.8 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was triturated with water
  4. customto give a powder
  5. customThe powder was recrystallized from ethanol

Sources & evidence

ORD record
ord-0d6e7061eafa41a7aff91312826b9946
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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