Acetic Acid → 2-Benzoylamino-4-methyl-thiazole-5-carboxylic acid

HRID 45320

Reaktionsgleichung

Reaktionsgleichung von HRID 45320
[C:1]([NH:9][C:10]1[S:11][C:12]([C:16]([O:18]CC)=[O:17])=[C:13]([CH3:15])[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].C(O)(=O)C>O1CCCC1.O>[C:1]([NH:9][C:10]1[S:11][C:12]([C:16]([OH:18])=[O:17])=[C:13]([CH3:15])[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 683991Ethyl 2-benzamido-4-methylthiazole-5-carboxylate

Produkt 1

HCID 8568022-Benzoylamino-4-methyl-thiazole-5-carboxylic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of ethyl 2-benzamido-4-methylthiazole-5-carboxylate (3.00 g, 10.00 mmol) and lithium hydroxide (2.50 g, 103.00 mmol) in a mixture of tetrahydrofuran (40 mL) and water (10 mL) was stirred at 50° C. for 20 h. The mixture was then cooled to 0° C. and neutralized with acetic acid to pH 7. The precipitate obtained was collected by filtration, washed with water and dried in vacuo to afford the title compound as a white solid in 75% yield (2.0 g); 1H NMR (DMSO-d6, 300 MHz) δ 12.92 (s, br, 1H), 8.06-8.04 (m, 2H), 7.63-7.48 (m, 3H), 2.53 (s, 3H).

Aufarbeitung

  1. customThe precipitate obtained
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b9d608bfbfb4ec09b8d68917a266b79
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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