Sodium Hydroxide → 2-(3,4-Dimethoxyphenyl)-4-fluoro-1,3-benzothiazole

HRID 131621

反応式

HRID 131621 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:20])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[OH-].[Na+]>O.C(O)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[F:1][C:2]1[C:3]2[N:8]=[C:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)[S:20][C:4]=2[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 11702019HCID 11702019、化合物

生成物 1

HCID 117019992-(3,4-Dimethoxyphenyl)-4-fluoro-1,3-benzothiazole収率 55%

試薬・触媒・溶媒 3

HCID 178511488HCID 178511488、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
95 °C

実験手順

A solution of N-(2-fluorophenyl)-3,4-dimethoxythiobenzamide (0.850 g, 2.92 mmol) and sodium hydroxide (0.93 g, 23.3 mmol) in water (10 mL) and ethanol (0.5 mL) was added dropwise to a solution of potassium ferricyanide (3.84 g, 11.7 mmol) in water (5 mL) at 95° C. The resulting solution was stirred at 95° C. for a further 2 h and then cooled in an ice bath. The precipitate was collected by vacuum filtration, washed with water and dissolved in ethyl acetate (10 mL) and insoluble material was removed by filtration. The filtrate was concentrated in vacuo and the crude product purified by column chromatography (dichloromethane) to give the required product as a pale yellow powder (0.46 g, 55% yield), mp 129° C.; 1H NMR (DMSO-d6) δ 7.95 (1H, m, ArH), 7.65 (2H, m, ArH), 7.42 (2H, m, ArH), 7.15 (1H, m, ArH), 3.90 (3H, s, OMe), 3.88 (3H, s, OMe); m/z (CI) 290 (M++1); Anal. (C15H12FNO2S) C, H, N. C: found 62.36%, calc. 62.27%; H: found 4.19%, calc.4.18%; N: found 4.93%, calc. 4.84%.

後処理

  1. temperaturecooled in an ice bath
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate (10 mL)
  5. custominsoluble material was removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude product purified by column chromatography (dichloromethane)

出典と根拠

ORDレコード
ord-4ad773408e8644349028421071ca49fb
出典データセット
uspto-grants-2008_06
特許番号
US07384966B2

関連ノート

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