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

HRID 1087226
Notes
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Reaction equation

HRID 1087226 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]([NH: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[NH: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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10472404HCID 10472404, compound

Product 1

HCID 867449342'-(2,4-Difluorophenylamino)-4'-[1-(methoxyimino)ethyl]methanesulfonanilideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-acetyl-2'-(2,4-difluorophenylamino)methanesulfonanilide (1.5 g), methoxylamine hydrochloride (0.4 g) and pyridine (0.43 ml) in ethanol (15 ml) was refluxed for 3 hours. The mixture was cooled to room temperature. Precipitates were filtered, washed with water, and recrystallized from ethanol to give colorless needles of 2'-(2,4-difluorophenylamino)-4'-[1-(methoxyimino)ethyl]methanesulfonanilide (1.4 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customPrecipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6650ed37eac644a193e0831e9cfd4fac
Source dataset
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05034417

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes