Dimethyl Sulfate → Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

HRID 1373194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373194
[F:1][C:2]1[C:3]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[F:11])[C:5]([OH:7])=[O:6].[C:24](=O)(O)[O-].[Na+].COS(OC)(=O)=O.CCCCCC>CC(C)=O.CCOC(C)=O>[CH3:24][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]([F:11])=[C:2]([F:1])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23]

Komponenten

7

Edukt 4

HCID 6497Dimethyl SulfateHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 210742923,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

Produkt 1

HCID 58781115Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-nitro-benzoic acid (595.3 g, 1.363 mol) in acetone (9 L) was added sodium bicarbonate (609.0 g, 3.48 mol) and the mixture was stirred for 10 min. To this suspension was added dimethylsulfate (285.6 ml, 3.026 mol) and refluxed for 3 h (completion of reaction was confirmed by TLC-hexane: EtOAc/4:1), cooled to room temperature and evaporated under vacuum. The residue (yellow) was further digested in hot methanol (2 L), filtered, washed with methanol and dried to give the title compound as a solid (yellow). Yield: 405.63g (65.54%).

Aufarbeitung

  1. temperaturerefluxed for 3 h
  2. customevaporated under vacuum
  3. filtrationfiltered
  4. washwashed with methanol
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-558c4bb42bc54c82a1524ebc74602d7d
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160915B2

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