Methanol → 2-Sulfanyl-1,3-benzoxazole-6-carboxylic acid

HRID 1692029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692029
[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:4]=2[O:3]1.[OH-].[K+].O1CCCC1.CO>C(OCC)(=O)C.O>[S:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:4]=2[O:3]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 45789990Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate

Produkt 1

HCID 207347702-Sulfanyl-1,3-benzoxazole-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Methyl 2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate (Example 92A, 470 mg, 2.25 mmol) and potassium hydroxide (1.26 g, 22.5 mmol) were combined in a 11.6 mL mixture of tetrahydrofuran, methanol, and water (10:1:1) and stirred at 45° C. for three hours. The reaction mixture was diluted with ethyl acetate, washed with a 1 N aqueous solution of hydrochloric acid, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound. MS (ESI−) m/z 193.8 (M−H)−.

Aufarbeitung

  1. washwashed with a 1 N aqueous solution of hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8d9d3b0756ed49c59935c330692855ad
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153813B2

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