Sulfuric Acid → 3-[5-(2-Amino-4-pyridyl)-2-ethyl-1,3-thiazol-4-YL]benzoic acid

HRID 1727372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727372
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#N)[CH:16]=2)[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:24].[OH-:28].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[C:21]([OH:24])=[O:28])[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 229327263-[5-(2-Aminopyridin-4-yl)-2-ethyl-1,3-thiazol-4-yl]benzonitrile

Produkt 1

HCID 534254603-[5-(2-Amino-4-pyridyl)-2-ethyl-1,3-thiazol-4-YL]benzoic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 5-(2-amino-4-pyridyl)-4-(3-cyanophenyl)-2-ethyl-1,3-thiazole (0,50 g, 1.6 mmol) in acetic acid (5 mL) was added 50% sulfuric acid (2.0 mL), and the mixture was stirred for 6 hours at 110° C. The reaction mixture was basified with aqueous sodium hydroxide solution and washed with ethylacetate. The aqueous phase was neutralized with hydrochloric acid, and the deposited crystal was washed with water and ethyl ether to obtain a title compound (0.45 g, yield 84%).

Aufarbeitung

  1. washwashed with ethylacetate
  2. washthe deposited crystal was washed with water and ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8b7c3f3e211c4ab2b7656758f6d2b39b
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

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