Lithium hydroxide, monohydrate → 4-(4-Nitrophenyl)thiazole-2-carboxylic acid

HRID 1024432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024432
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]([O:17]CC)=[O:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.[OH-].[Li+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([C:15]([OH:17])=[O:16])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 10084925Ethyl 4-(4-nitrophenyl)-1,3-thiazole-2-carboxylate2×

Produkt 1

HCID 152742424-(4-Nitrophenyl)thiazole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To ethyl 4-(4-nitrophenyl)thiazole-2-carboxylate (Intermediate 3, step A, 7.0 g) in THF (70 ml) was added (1 ml) 1N lithium hydroxide monohydrate solution and reaction mixture was stirred for 4 hours at RT. Organic solvent was concentrated, water was added, and the reaction mixture was made acidic by dilute HCl solution. This resulted in precipitation of white solid, which was filtered and washed with water. The solid was dried to obtain the title compound. Yield: 6.2 gm (98%). 1H NMR (DMSO-d6, 300 MHz): δ 8.78 (s, 1H), 8.32 (d, 4H).

Aufarbeitung

  1. concentrationOrganic solvent was concentrated
  2. additionwater was added
  3. customThis resulted in precipitation of white solid, which
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-8f44e5169d0446bbb6ea100d619b50be
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

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