4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → Ethyl 4-[2-(2-chlorophenyl)hydrazino]-2-(methylthio)pyrimidine-5-carboxylate

HRID 545226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545226
C(N(CC)C(C)C)(C)C.Cl[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([S:22][CH3:23])[N:12]=1.Cl.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][NH2:33]>O1CCCC1>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][NH:33][C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([S:22][CH3:23])[N:12]=1

Komponenten

5

Edukt 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 4432872-Chlorophenylhydrazine hydrochloride

Produkt 1

HCID 67171554Ethyl 4-[2-(2-chlorophenyl)hydrazino]-2-(methylthio)pyrimidine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At room temperature, 16.2 mL of N,N-diisopropylethylamine was added to tetrahydrofuran (300 mL) solution of 9.4 g of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate and 8.3 g of 2-chlorophenylhydrazine hydrochloride, and heated under reflux for 18 hours. The solvent was concentrated under reduced pressure, water was added to this, and extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain crude ethyl 4-[2-(2-chlorophenyl)hydrazino]-2-(methylthio)pyrimidine-5-carboxylate as a yellow oily substance.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe solvent was concentrated under reduced pressure, water
  4. additionwas added to this, and
  5. extractionextracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with saturated saline water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe solvent was evaporated away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-48d5b8a2b45f43f19f7c8741247eb5ef
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935708B2

Notizen zur Reaktion

Wird geladen…