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

HRID 605188
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HRID 605188 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-94247b29927e40e499a37d9caf969200
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910595B2

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