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

HRID 605188Notes

Reaction equation

HRID 605188 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-94247b29927e40e499a37d9caf969200
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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