4-Ethoxyphenylthiourea → N-(4-Ethoxyphenyl)-4-(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)-1,3-thiazol-2-amine;hydrobromide

HRID 889228

Reaktionsgleichung

Reaktionsgleichung von HRID 889228
Br.[Br:2][CH2:3][C:4]([C:6]1[N:13]2[C:9]([S:10][CH:11]=[CH:12]2)=[N:8][C:7]=1[CH3:14])=O.[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH2:27])=[S:26])=[CH:20][CH:19]=1)[CH3:16]>C(O)C>[BrH:2].[O:17]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]2[S:26][CH:3]=[C:4]([C:6]3[N:13]4[C:9]([S:10][CH:11]=[CH:12]4)=[N:8][C:7]=3[CH3:14])[N:27]=2)=[CH:20][CH:19]=1)[CH2:15][CH3:16]

Komponenten

4

Edukt 2

HCID 8535694-EthoxyphenylthioureaHCID 866278482-Bromo-1-(6-methylimidazo[2,1-b]thiazol-5-yl)ethanone hydrobromide

Produkt 1

HCID 2877568N-(4-Ethoxyphenyl)-4-(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)-1,3-thiazol-2-amine;hydrobromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-1-(6-methylimidazo[2,1-b]thiazol-5-yl)ethanone hydrobromide (18) (2.20 g, 6.5 mmol) and (p-ethoxyphenyl)thiourea (10) (1.30 g, 6.5 mmol) in 40 mL of anhydrous ethanol was refluxed under stirring for 20 h, and then cooled to room temperature. The solid was filtered. The crude white solid product was re-crystallized from methanol. The methanol solution was filtered while still hot to remove possible dust, and then heated into solution. It was re-crystallized two more times from methanol, and dried under vacuum to provide the desired product 20 as a white solid, yield 0.64 g (22.4%), HPLC purity 97.81%, mp >240° C. 1HNMR (CD3OD) δ 1.27 (t, 3H, J=6.8 Hz), 2.56 (s, 3H), 3.88-3.94 (m, 2H), 6.85 (d, 2H, J=8.8 Hz), 6.97 (s, 1H), 7.34 (d, 2H, J=8.8 Hz), 7.54 (d, 1H, J=4.4 Hz), 8.44 (d, 1H, J=4.4 Hz). ESI-MS m/z 357 (M+1)+.

Aufarbeitung

  1. temperaturewas refluxed
  2. filtrationThe solid was filtered
  3. customThe crude white solid product was re-crystallized from methanol
  4. filtrationThe methanol solution was filtered while still hot
  5. customto remove possible dust
  6. temperatureheated into solution
  7. customIt was re-crystallized two more times from methanol
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-20895cacf9754a578ed0cb7f679b5719
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252822B2

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