Sulfuric Acid → HCID 59164407, Verbindung

HRID 1441615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441615
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][F:11])=[CH:6][C:5]=1[NH:12]C(=O)C.S(=O)(=O)(O)O>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][F:11])=[CH:6][C:5]=1[NH2:12]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 59164463HCID 59164463, Verbindung

Produkt 1

HCID 59164407HCID 59164407, VerbindungAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-acetylamino-4-fluoromethyl-benzoic acid methyl ester (1.5 g, 6.66 equiv) in MeOH (50 mL) was added concd sulfuric acid (4 mL) and the mixture was refluxed for 1 h. The mixture was cooled down and concentrated in vacuo. Water was added and the pH was adjusted to 9-10 by addition of 2N NaOH. The aqueous phase was extracted with AcOEt. The organic phase were combined, washed with brine and dried (Na2SO4). The solution was concentrated in vacuo to afford the title compound as a yellow-orange oil (1.24 g, 100%) (ES-MS: m/z 184.1 [M+H]+, rt 4.91 min).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 h
  2. temperatureThe mixture was cooled down
  3. concentrationconcentrated in vacuo
  4. additionWater was added
  5. additionthe pH was adjusted to 9-10 by addition of 2N NaOH
  6. extractionThe aqueous phase was extracted with AcOEt
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8343c6d61344f448857a650209ad452
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655666B2

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