Sodium Hydroxide → 2-Amino-4-methyl-thiazole-5-carboxylic acid

HRID 560533

Reaktionsgleichung

Reaktionsgleichung von HRID 560533
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10]CC)=[O:9])=[C:5]([CH3:7])[N:6]=1.[OH-].[Na+]>O1CCCC1.O>[NH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Produkt 1

HCID 8322432-Amino-4-methyl-thiazole-5-carboxylic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.5 mmol) and NaOH (5.40 g, 135 mmol) in tetrahydrofuran (60 mL) and water (30 mL) was heated to reflux overnight. Tetrahydrofuran was removed in vacuo, and the residue was neutralized with 5% hydrochloric acid solution to pH 5˜6. The precipitate obtained was collected by filtration and dried to afford the crude 2-amino-4-methylthiazole-5-carboxylic acid (5.20 g, 94%): 1H NMR (300 MHz, DMSO-d6) δ 7.63 (s, 2H), 2.30 (s, 3H); MS (ES+) m/z 159.1 (M+1).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customTetrahydrofuran was removed in vacuo
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-45fc3713ccff472292b5824c2dd98953
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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