Methanesulfonic Acid → 3-((3-(4-Chloro-2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide

HRID 453123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453123
C([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21][O:22][C:23]2[C:24]([F:33])=[C:25]([C:29]([F:32])=[CH:30][CH:31]=2)[C:26]([NH2:28])=[O:27])[S:18][N:17]=1)C1C=CC=CC=1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([C:16]2[N:20]=[C:19]([CH2:21][O:22][C:23]3[C:24]([F:33])=[C:25]([C:29]([F:32])=[CH:30][CH:31]=3)[C:26]([NH2:28])=[O:27])[S:18][N:17]=2)=[C:9]([OH:8])[CH:14]=1

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 595495353-((3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide

Produkt 1

HCID 1358727333-((3-(4-Chloro-2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamideAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-((3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide (0.05 g, 0.10 mmol) in dichloromethane (5 ml) was added methanesulfonic acid (0.50 ml, excess) at room temperature under nitrogen atmosphere and allowed to stir at same temperature for 90 min. After the completion of the reaction (TLC monitoring), the solution was cooled to 0° C. and basified with saturated NaHCO3 solution (aqueous) followed by extraction with EtOAc (3×25 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated. The residue was washed with ether to get the desired product (0.012 g, 30%).

Aufarbeitung

  1. customAfter the completion of the reaction (TLC monitoring)
  2. extractionfollowed by extraction with EtOAc (3×25 ml)
  3. dry with materialThe combined organics was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-b2a9751877294b129ea2d909eee6264a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492414B2

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