Sodium Hydroxide → 4-Methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acid

HRID 45316

Reaktionsgleichung

Reaktionsgleichung von HRID 45316
[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][N:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.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][N:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 719362Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate

Produkt 1

HCID 822263324-Methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate (1.46 g, 5.0 mmol) and sodium hydroxide (0.40 g, 10.00 mmol) in methanol (100 mL) and water (25 mL) was stirred at ambient temperature overnight and then heated to reflux for 2 h. The mixture was concentrated and then neutralized with 5% hydrochloric acid solution to pH 5˜6. The precipitate obtained was collected by filtration and dried to give the title compound in 89% yield (1.17 g); 1H NMR (DMSO-d5, 300 MHz) δ 8.74 (d, J=6.0 Hz, 2H), 7.93 (d, J=6.0 Hz, 2H), 2.46 (s, 3H); MS (ES+) m/z 264.1 (M+1).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b00f813201694d0c85e3131770ab7d6b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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