Lithium Hydroxide → 2-(4-Fluoro-2-nitroanilino)benzo[b]thiophene-3-carbonitrile

HRID 131367

反応式

HRID 131367 の反応式
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]#[N:12].F[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].[OH-].[Li+]>CS(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:1][C:2]2[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[C:3]=2[C:11]#[N:12])=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=1

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 677672,5-DifluoronitrobenzeneHCID 232735812-Amino-1-benzothiophene-3-carbonitrile

生成物 1

HCID 184222982-(4-Fluoro-2-nitroanilino)benzo[b]thiophene-3-carbonitrile収率 9.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Combine 2-amino-benzo[b]thiophene-3-carbonitrile (3.75 g, 21.5 mmol), 1,4-Difluoro-2-nitro-benzene (2.33 mL, 21.5 mmol), and lithium hydroxide (1.03 g, 43.0 mmol) in anhydrous dimethylsulfoxide (50 mL), and heat at 55° C. for about 5 hours. Cool to ambient temperature, pour into a beaker filled with ice/deionized water (200 mL), and stir for 30 minutes. Isolate the precipitated material by suction filtration, wash the solid with dichloromethane, and dry it under reduced pressure to give the title compound (0.618 g). Add deionized water and ethyl acetate to the filtrate, and then separate the organic layer. Extract the aqueous layer with ethyl acetate many times, and then with dichloromethane many times. Then wash the organics with deionized water (3×). Combine the washes and back extract them with ethyl acetate. Wash the organics with a saturated solution of sodium chloride, and then dry (sodium sulfate), filter, and concentrate the organics under reduced pressure to a dark solid. After triturating with methanol, isolate the resulting solid by suction filtration, wash with methanol, and dry at ambient temperature under reduced pressure to give the title compound (4.422 g). Total solid: 5.04 g (74.8%): Mass spectrum (ES+, m/e): 314 (M+1); NMR (1H, 300 MHz, CDCl3), δ (ppm): 9.96 (s, 1H), 8.06-7.98 (m, 1H), 7.85-7.77 (m, 1H), 7.77-7.69 (m, 1H), 7.68-7.59 (m, 1H), 7.56-7.47 (m, 1H), 7.45-7.34 (m, 2H).

後処理

  1. additionpour into a beaker
  2. customIsolate the precipitated material
  3. filtrationby suction filtration
  4. washwash the solid with dichloromethane
  5. customdry it under reduced pressure

出典と根拠

ORDレコード
ord-40939a9deb6145adaa34c6eb040d29ee
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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