4-Aminothiophenol → HCID 66808383, compound

HRID 605437Notes

Reaction equation

HRID 605437 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([SH:29])=[CH:25][CH:24]=1.C([O-])(=O)C.[Na+]>C(O)C>[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][C:15]2[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)(=[O:11])=[O:10])=[CH:13][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 517045Sodium AcetateHCID 5016179HCID 5016179, compound

Product 1

HCID 66808383HCID 66808383, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of Example 458A (500 mg, 1.277 mmol), 4-aminothiophenol (240 mg, 1.915 mmol) and anhydrous sodium acetate (524 mg, 6.384 mmol) in anhydrous ethanol (9 mL) was heated at reflux under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature and the ethanol removed by rotary evaporation under vacuum. The residue was taken up in ethyl acetate (100 mL) and washed with water (2×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum, Co-evaporating the oil with methylene chloride/hexanes to obtain the title compound as an orange foam (613 mg, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 1 hour
  3. customthe ethanol removed by rotary evaporation under vacuum
  4. washwashed with water (2×50 mL) and brine (50 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum, Co-
  8. customevaporating the oil with methylene chloride/hexanes

Sources & evidence

ORD record
ord-fef93376c56e4a5d9e4f92279f88b684
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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