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

HRID 131621

반응식

HRID 131621 반응식
[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

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 11702019HCID 11702019, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 178511488HCID 178511488, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
95 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-4ad773408e8644349028421071ca49fb
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384966B2

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