Lithium Hydroxide → 2-Benzoylamino-4-phenylthiazole-5-carboxylic Acid

HRID 45317

Reaktionsgleichung

Reaktionsgleichung von HRID 45317
[C:1]([NH:9][C:10]1[S:11][C:12]([C:21]([O:23]CC)=[O:22])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.O>[C:1]([NH:9][C:10]1[S:11][C:12]([C:21]([OH:23])=[O:22])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 4304712Ethyl 2-benzamido-4-phenylthiazole-5-carboxylate

Produkt 1

HCID 866425142-Benzoylamino-4-phenylthiazole-5-carboxylic AcidAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-benzamido-4-phenylthiazole-5-carboxylate (1.62 g, 4.60 mmol) and lithium hydroxide (0.96 g, 23.00 mmol) was stirred at 50° C. in tetrahydrofuran/water mixture for 96 h. The organic solvent was removed in vacuo and the water layer was washed with ethyl acetate and then acidified by the addition of 15% hydrochloric acid solution to pH 5. The white precipitate obtained was collected by filtration and dried to afford 0.89 g of the title compound in 59% yield; 1H NMR (CDCl3, 300 MHz) δ 13.05 (s, 1H), 8.09 (d, J=7.1 Hz, 2H), 7.80-7.35 (m, 8H); MS (ES+) m/z 325.1 (M+1).

Aufarbeitung

  1. customThe organic solvent was removed in vacuo
  2. washthe water layer was washed with ethyl acetate
  3. additionacidified by the addition of 15% hydrochloric acid solution to pH 5
  4. customThe white precipitate obtained
  5. filtrationwas collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e577a7b84ba94dfb99743d1cdc94bb42
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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