Acetic Acid → 1,3-Benzenediol,5-[5-(trifluoromethyl)-2-benzothiazolyl]-

HRID 1748972

Reaktionsgleichung

Reaktionsgleichung von HRID 1748972
C(O)(=O)C.[NH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[SH:16].[OH:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([OH:26])[CH:25]=1)[CH:21]=O.C([O-])(=O)C.[Na+]>O.C(OCC)(=O)C>[F:15][C:12]([F:13])([F:14])[C:10]1[CH:9]=[CH:8][C:7]2[S:16][C:21]([C:20]3[CH:23]=[C:24]([OH:26])[CH:25]=[C:18]([OH:17])[CH:19]=3)=[N:5][C:6]=2[CH:11]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 880422-Amino-4-(trifluoromethyl)benzenethiolHCID 943653,5-DihydroxybenzaldehydeHCID 517045Sodium Acetate

Produkt 1

HCID 601945801,3-Benzenediol,5-[5-(trifluoromethyl)-2-benzothiazolyl]-Ausbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In an acetic acid (0.42 mL) solvent, a mixture including 2-amino-4-(trifluoromethyl)benzenethiol (100 mg, 0.44 mmol), 3,5-dihydroxybenzaldehyde (60 mg, 0.44 mmol), and sodium acetate (107 mg, 1.30 mmol) was refluxed for 6.5 hours. After cooling, the reaction mixture was distributed between ethyl acetate and water, and an organic layer was dried by using MgSO4, filtered, and evaporated under reduced pressure. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (2:1) as a developer to obtain a solid Compound 36 (50.6 mg, 37%).

Aufarbeitung

  1. temperaturewas refluxed for 6.5 hours
  2. temperatureAfter cooling
  3. customan organic layer was dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residual was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-938ccd8bdade46769b3ee5fe67fced04
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09155690B2

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