Phosphorus trichloride → 2-Amino-5-(4-pyridyl)-4-[(4-piperonyl-1-piperazinyl)carbonyl]thiazole

HRID 648590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648590
[CH2:1]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.P(Cl)(Cl)Cl.[NH2:21][C:22]1[S:23][C:24]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:25]([C:27](O)=[O:28])[N:26]=1>N1C=CC=CC=1>[NH2:21][C:22]1[S:23][C:24]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:25]([C:27]([N:14]2[CH2:15][CH2:16][N:11]([CH2:1][C:2]3[CH:10]=[CH:9][C:8]4[O:7][CH2:6][O:5][C:4]=4[CH:3]=3)[CH2:12][CH2:13]2)=[O:28])[N:26]=1

Komponenten

5

Edukt 3

HCID 24387Phosphorus trichlorideHCID 944261-PiperonylpiperazineHCID 201449862-Amino-5-(pyridin-4-yl)-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 201450812-Amino-5-(4-pyridyl)-4-[(4-piperonyl-1-piperazinyl)carbonyl]thiazoleAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 1-piperonylpiperazine (2.72 g) and phosphorus trichloride (0.49 ml) in pyridine (20 ml) was added 2-amino-5-(4-pyridyl)-4-thiazolecarboxylic acid (1.24 g) and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The resultant mixture was adjusted to pH 8.0 with saturated aqueous potassium carbonate. The organic extract was dried over magnesium sulfate. The solvent was evaporated in vacuo to give a crystalline residue, which was recrystallized from ethyl acetate to afford 2-amino-5-(4-pyridyl)-4-[(4-piperonyl-1-piperazinyl)carbonyl]thiazole (0.45 g). mp 216°-217° C.

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customto give a crystalline residue, which
  7. customwas recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1fb820e14d0449cf8bd37a69fee45a8d
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04735957

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