Flufenamic Acid → HCID 15678604, Verbindung

HRID 2211179

Reaktionsgleichung

Reaktionsgleichung von HRID 2211179
[CH:1]1[CH:2]=[CH:3][C:4]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)=[C:5]([C:7](O)=[O:8])[CH:6]=1.[NH2:21][NH:22][C:23]([NH2:25])=[S:24]>O1CCCC1.N1C=CC=CC=1>[NH2:25][C:23](=[S:24])[NH:22][NH:21][C:7](=[O:8])[C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=1[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1

Komponenten

5

Edukt 2

HCID 3371Flufenamic AcidHCID 2723789Thiosemicarbazide

Produkt 1

HCID 15678604HCID 15678604, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N,N'-Carbonyldiimidazole (4.56 g, 27.6 mmoles) is added to a room temperature solution of flufenamic acid (5.07 g, 18.0 mmoles) in 70 ml of tetrahydrofuran. The clear yellow solution is stirred at room temperature for three hours. The solution is then added via cannula to a suspension of thiosemicarbazide (3.41 g, 37.5 mmoles) in 55 ml of pyridine. The suspension is heated at reflux overnight. The clear orange solution is concentrated in vacuo, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with additional water, dried over magnesium sulfate, and concentrated. The resulting solid is slurried with a 1:3 mixture of ethyl acetate and hexane. The off-white solid is collected by filtration providing 2.80 g (44%) of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide.

Aufarbeitung

  1. temperatureThe suspension is heated
  2. temperatureat reflux overnight
  3. concentrationThe clear orange solution is concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate and water
  5. washThe organic layer is washed with additional water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. additionThe resulting solid is slurried with a 1:3 mixture of ethyl acetate and hexane
  9. filtrationThe off-white solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5b7b7ed4bdd34e7583b1e0bcefe756e5
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05462952

Verknüpfte Notizen

Wird geladen…