Water → 2-(2-Nitro-4-trifluoromethyl-phenylamino)-benzo[b]thiophene-3-carbonitrile

HRID 131368

反応式

HRID 131368 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]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25].[OH-].[Li+].O>CS(C)=O.ClCCl>[N+:24]([C:15]1[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:14]=1[NH: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])([O-:26])=[O:25]

参加物

7

反応物 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 232735812-Amino-1-benzothiophene-3-carbonitrile

生成物 1

HCID 586260492-(2-Nitro-4-trifluoromethyl-phenylamino)-benzo[b]thiophene-3-carbonitrile収率 63.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

Combine 2-amino-benzo[b]thiophene-3-carbonitrile (3.48 g, 20.0 mmol), 1-Fluoro-2-nitro-4-trifluoromethyl-benzene (4.31 g, 20.0 mmol), and lithium hydroxide (0.958 g, 40.0 mmol) in anhydrous dimethylsulfoxide (50 mL), and heat at 55° C. for 2 hours. Cool to ambient temperature, pour into a beaker filled with ice/deionized water (50 mL), and stir for 30 minutes. Add deionized water and dichloromethane and then separate the organic layer. Extract the aqueous layer with dichloromethane many times. Then wash the organics with deionized water (3×). Combine the washes and back extract them with dichloromethane. Wash the organics with a saturated solution of sodium chloride, and back extract the combined washes with dichloromethane. Dry (sodium sulfate), filter, and concentrate the organics under reduced pressure to a residue. After triturating the residue 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 (4.61 g). Concentrate the filtrate under reduced pressure and purify by flash chromatography, eluting with a gradient of ethyl acetate: dichloromethane: hexane (0.25:5:5, 0-100% in hexane) to give the title compound (0.53 g). Total solid: 5.14 g (70.8%). NMR (1H, 300 MHz, CDCl3), δ (ppm): 10.26 (s, 1H), 8.63-8.56 (m, 1H), 7.93-7.85 (m, 1H), 7.84-7.75 (m, 2H), 7.64-7.45 (m, 3H).

後処理

  1. additionpour into a beaker
  2. customseparate the organic layer
  3. extractionExtract the aqueous layer with dichloromethane many times
  4. washThen wash the organics with deionized water (3×)
  5. extractionCombine the washes and back extract them with dichloromethane
  6. washWash the organics with a saturated solution of sodium chloride
  7. extractionback extract the combined washes with dichloromethane
  8. dry with materialDry (sodium sulfate)
  9. filtrationfilter
  10. concentrationconcentrate the organics under reduced pressure to a residue
  11. customAfter triturating the residue with methanol
  12. customisolate the resulting solid
  13. filtrationby suction filtration
  14. washwash with methanol
  15. customdry at ambient temperature under reduced pressure

出典と根拠

ORDレコード
ord-78e752b0bec446ccbbf7a9fa085f7d9d
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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