4-Aminothiophenol → 4-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamide

HRID 605054

反応式

HRID 605054 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+]>C(O)C>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[O:20])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 145104-AminothiophenolHCID 517045Sodium AcetateHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamide

生成物 1

HCID 670408504-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamide収率 87.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of the product of Example 10A (1.00 g, 2.816 mmol), 4-aminothiophenol (529 mg, 4.224 mmol) and anhydrous sodium acetate (1.155 g, 14.08 mmol) in anhydrous ethanol (30 mL) was heated at reflux under a nitrogen atmosphere for 19 hours. The reaction was cooled to room temperature and the ethanol removed by rotary evaporation. The residue was taken up in water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration of the solid with 4% ethyl acetate/methylene chloride (25 mL) afforded the title compound as a yellow solid (1.091 g, 87%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 19 hours
  3. customthe ethanol removed by rotary evaporation
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f6cd7585c1f84199a0a4c25985e5e4a4
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

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