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

HRID 889228

反応式

HRID 889228 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-20895cacf9754a578ed0cb7f679b5719
出典データセット
uspto-grants-2012_08
特許番号
US08252822B2

関連ノート

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