Methanol → 2-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylthiophenyl) thiazole

HRID 1378597ノート

反応式

HRID 1378597 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)Br.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[S:24].CO>C(O)C>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]1[S:24][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:25]=1

参加物

5

反応物 3

HCID 887MethanolHCID 27348242-ChlorothiobenzamideHCID 537994631-(2-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromo ethanone

生成物 1

HCID 539795112-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylthiophenyl) thiazole収率 79.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 1-(2-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone from Step 3 (1.39 g, 4.1 mmol) and 2-chlorothiobenzamide (0.71 g, 4.1 mmol) in 10 mL of ethanol was heated to reflux for 4.4 hours. The solution was cooled to room temperature and poured into 25 mL of methanol, chilled with an ice bath whereupon crystals of pure product formed which were isolated by filtration and air dried to afford the thiazole (1.34 g, 79%): mp 117°-119° C. 1H NMR (CDCl3) 300 MHz 8.37 (m, 1H), 7.62 (m, 2H), 7.49 (d, J=7.7Hz,1H), 7.32 (m, 7H), 7.22 (d, J=8.5Hz, 2H), 2.51 (s, 3H). Mass spectrum M+ +H=412.

後処理

  1. temperatureto reflux for 4.4 hours
  2. temperaturechilled with an ice bath whereupon crystals of pure product
  3. customformed which
  4. customwere isolated by filtration and air
  5. customdried

出典と根拠

ORDレコード
ord-b701e2d725d546379db794ba1ebfcbe9
出典データセット
uspto-grants-1997_09
特許番号
US05668161

反応ノート

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