2-(2-Chlorophenoxy)ethanethioamide → HCID 54014773、化合物

HRID 1378600ノート

反応式

HRID 1378600 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)Br)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[O:23][CH2:24][C:25]([NH2:27])=[S:26]>C(#N)C.CO>[Cl:20][C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[O:23][CH2:24][C:25]1[S:26][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:27]=1

参加物

5

反応物 2

HCID 27435522-(2-Chlorophenoxy)ethanethioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

生成物 1

HCID 54014773HCID 54014773、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone (2.05 g, 6.04 mmol) (Example 1, Step 3) and 2-chlorophenoxy thioacetamide (1.21 g, 6.0 mmol) in 30 mL of acetonitrile was heated to reflux for 3 hours. The solution was diluted with methanol, cooled to 0° C. in an ice bath and a precipitate formed that was removed by filtration. The crude solid was further purified by flash chromatography over silica gel and the appropriate fractions were combined, concentrated in vacuo and crystallized from methanol to provide 2.60 g (98%) of pure 4-2- ((2 -chlorophenoxy) methyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl) thiazole: mp 126°-129° C., 1H NMR (CDCl3) 300 MHz 7.55-7.39 (m, 4H), 7.28-6.90 (m, 8H), 5.44 (s, 2H), 2.49 (s, 3H). 19F NMR (CDCl3) -114.00 (m). Mass spectrum M+H+ =442.

後処理

  1. temperatureto reflux for 3 hours
  2. customa precipitate formed
  3. customthat was removed by filtration
  4. customThe crude solid was further purified by flash chromatography over silica gel
  5. concentrationconcentrated in vacuo
  6. customcrystallized from methanol

出典と根拠

ORDレコード
ord-f90fb59fd7e84caca5fb0bea9679fe43
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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