2-Aminothiazole → Imidazo[2,1-b]thiazole,5-[4-(methylsulfonyl)phenyl]-6-phenyl-

HRID 741682ノート

反応式

HRID 741682 の反応式
[C:1]1([C:7](=O)[CH:8](Br)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])(O)=O.[Na+]>CCO>[CH3:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([C:8]2[N:26]3[C:22]([S:23][CH:24]=[CH:25]3)=[N:21][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:10][CH:11]=1)(=[O:17])=[O:16]

参加物

5

反応物 3

HCID 21552-AminothiazoleHCID 516892Sodium BicarbonateHCID 153152121-Phenyl-2-bromo-2-(4-(methylsulfonyl)phenyl)ethanone

生成物 1

HCID 9928539Imidazo[2,1-b]thiazole,5-[4-(methylsulfonyl)phenyl]-6-phenyl-収率 44.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of the bromoketone of step 3 (2.26 g, 6.4 mmol) and 2-aminothiazole (964 mg, 9.6 mmol) in EtOH (45 mL) was heated to reflux for 18 h. Aqueous NaHCO3 was added to the cooled mixture and the mixture was extracted with Et2O. The Et2O extracts were washed with brine, dried over MgSO4, filtered and concentrated to an oil. Chromatography of the oil on silica gel (eluted with 60 % EtOAc/hexane) gave 1 g (44%) of the title compound: m.p. 190°-192° C. Anal. calcd for C18H14N2O2S2 : C, 61.00; H, 3.98; N, 7.90. Found: C, 60.31; H, 3.96; N, 7.68. 1H NMR (CD3COCD3): δ3.20 (s, 3H), 7.20-7.34 (m, 4H), 7.58-7.61 (m, 2H), 7.77-7.83 (m, 3H), 8.03-8.06 (m, 2H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. extractionthe mixture was extracted with Et2O
  4. washThe Et2O extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

出典と根拠

ORDレコード
ord-cb075af8373741bc90c99770b980ef22
出典データセット
uspto-grants-1996_09
特許番号
US05552422

反応ノート

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