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

HRID 889228

반응식

HRID 889228 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-20895cacf9754a578ed0cb7f679b5719
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252822B2

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