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4-Aminothiophenol → 4-(4-Amino-phenylsulfanyl)-N-(5-tert-butyl-thiazol-2-yl)-3-nitro-benzamide

HRID 605188
ノート
印刷プレビュー

反応式

HRID 605188 の反応式
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+]>C(O)C>[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][C:15]2[CH:16]=[CH:17][C:12]([C:11]([NH:10][C:8]3[S:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][N:7]=3)=[O:22])=[CH:13][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:26][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 145104-AminothiophenolHCID 517045Sodium AcetateHCID 86615551N-(5-tert-Butyl-thiazol-2-yl)-4-chloro-3-nitro-benzamide

生成物 1

HCID 866155524-(4-Amino-phenylsulfanyl)-N-(5-tert-butyl-thiazol-2-yl)-3-nitro-benzamide収率 72%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of the product of Example 161A (500 mg, 1.472 mmol), 4-aminothiophenol (350 mg, 2.796 mmol) and anhydrous sodium acetate (604 mg, 7.36 mmol) in anhydrous ethanol (15 mL) was heated at reflux under a nitrogen atmosphere for 3 hours. The reaction was cooled to room temperature and the ethanol removed by rotary evaporation. The residue was partitioned with water (50 mL) and ethyl acetate (100 mL), and the organic phase washed with water (2×50 mL) and brine (50 mL). The organic extract was 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 (452 mg, 72%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 3 hours
  3. customthe ethanol removed by rotary evaporation
  4. customThe residue was partitioned with water (50 mL) and ethyl acetate (100 mL)
  5. washthe organic phase washed with water (2×50 mL) and brine (50 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-94247b29927e40e499a37d9caf969200
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07910595B2

反応ノート

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