Methanesulfonic Acid → HCID 12071999, Verbindung

HRID 49377

Reaktionsgleichung

Reaktionsgleichung von HRID 49377
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.CS(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl>[C:25]1([C:23]2[N:24]=[C:20]([C:17]3[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:19][CH:18]=3)[S:21][CH:22]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 12071998Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamate

Produkt 1

HCID 12071999HCID 12071999, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamate (396 mg, 0.92 mmol) was dissolved in methylene chloride (4.6 ml) and methanesulfonic acid (0.895 ml, 13.8 mmol) was added dropwise to give a homogenous yellow solution. The reaction mixture was allowed to stir for about sixteen hours, diluted with methylene chloride, and was brought to basic pH (12-13) with 1M sodium hydroxide. The mixture was then extracted with methylene chloride, and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride) to afford the product in 78% yield (213 mg). LRMS ([M+H]+)=297.2.

Aufarbeitung

  1. customto give a homogenous yellow solution
  2. extractionThe mixture was then extracted with methylene chloride
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude material was purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride)
  7. customto afford the product in 78% yield (213 mg)

Quellen und Nachweise

ORD-Eintrag
ord-a2226b9dd8a348c5915961ee284ee18f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706743B2

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