Ammonia → 6-[m-(1,3-Dimethylpyrazole-5-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

HRID 2166817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2166817
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][N:14]3[C:10]([S:11][CH2:12][CH2:13]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C[Al](C)C.C([O:22][C:23]([C:25]1[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=1)=O)C.Cl.N>ClCCl>[CH3:30][N:29]1[C:25]([C:23]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]3[CH2:15][N:14]4[C:10]([S:11][CH2:12][CH2:13]4)=[N:9]3)[CH:5]=[CH:6][CH:7]=2)=[O:22])=[CH:26][C:27]([CH3:31])=[N:28]1

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1385761,3-Dimethyl-5-ethoxycarbonylpyrazoleHCID 30386693-AminolevamisoleHCID 16682925Trimethylaluminum

Produkt 1

HCID 204979636-[m-(1,3-Dimethylpyrazole-5-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazoleAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (2.4 g, 11 mmol) in dry dichloromethane (30 ml) under nitrogen was added trimethylaluminium (4.8 ml; 25% in hexane). After 20 mins at room temperature 1,3-dimethylpyrazole-5-carboxylic acid ethyl ester (1.8 g, 11 mmol) in dry dichloromethane (1 ml) was added and the mixture heated under reflux for 24 hours. Hydrochloric acid (20 ml; 2 N aqueous) was added slowly, the resulting mixture basified with aqueous ammonia solution (5 N; 100 ml) and extracted with chloroform (3×200 ml) which after drying (MgSO4) and concentrating in vacuo afforded an oil. Separation of the oil on alumina eluting with chloroform gave the amide (1.28 g; 34%).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with chloroform (3×200 ml) which
  4. dry with materialafter drying (MgSO4)
  5. concentrationconcentrating in vacuo
  6. customafforded an oil
  7. customSeparation of the oil on alumina eluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-9929c6169ddc447588ffb1f896987a90
Quelldatensatz
uspto-grants-1983_06
Patentnummer
US04389406

Notizen zur Reaktion

Wird geladen…