Formic Acid → 5'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide

HRID 1085906

Reaktionsgleichung

Reaktionsgleichung von HRID 1085906
[C:1](OC(=O)C)(=O)C.C(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:24])[CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:14]([NH:25][CH3:26])[CH:13]=1.[OH2:27]>ClC(Cl)Cl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:24])[CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:14]([CH:13]=1)[N:25]([CH3:1])[CH:26]=[O:27]

Komponenten

6

Edukt 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 540378461-(4-Fluoro-2-methylaminophenyl)-2-methylsulphonylethanone

Produkt 1

HCID 867447425'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of acetic anhydride (19.8 ml) and formic acid (13.5 ml) was stirred and heated at 60° under nitrogen for 2 hours. 1-(4-Fluoro-2-methylaminophenyl)-2-methylsulphonylethanone (10.0 g), was added portionwise to the mixture at ambient temperature with stirring. The mixture was stirred at 30° for 30 minutes. Water (30 ml) was added to the reaction mixture which was then stirred at 30° for 30 minutes. Concentration of the reaction mixture by evaporation in vacuo gave a green oil. The oil was dissolved in trichloromethane (50 ml) and washed with aqueous sodium hydrogen carbonate solution (7% w/w; 2×30 ml). The trichloromethane extract was dried (magnesium sulphate) and evaporated in vacuo to give a green oil which solidified at ambient temperature. Recrystallisation from toluene gave 5'-fluoro-N-methyl-2'-methylsulphonylacetylformanilide, m.p. 94.5°-95.5°.

Aufarbeitung

  1. temperatureheated at 60° under nitrogen for 2 hours
  2. stirringwith stirring
  3. stirringThe mixture was stirred at 30° for 30 minutes
  4. stirringwas then stirred at 30° for 30 minutes
  5. customConcentration of the reaction mixture by evaporation in vacuo
  6. customgave a green oil
  7. washwashed with aqueous sodium hydrogen carbonate solution (7% w/w; 2×30 ml)
  8. extractionThe trichloromethane extract
  9. dry with materialwas dried (magnesium sulphate)
  10. customevaporated in vacuo
  11. customto give a green oil which
  12. customsolidified at ambient temperature
  13. customRecrystallisation from toluene

Quellen und Nachweise

ORD-Eintrag
ord-40e826fdf0a0493684ab04e6140c33c8
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05011931

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