2-Aminothiophenol → HCID 58389340, compound

HRID 2170600Notes

Reaction equation

HRID 2170600 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=O)[CH:13]=[N:14][CH:15]=1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([C:16]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 58389340HCID 58389340, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-aminothiophenol (500 mg, 3.99 mmol) and 5-bromo-3-pyridinecarboxaldehyde (743 mg, 3.99 mmol) was added ethanol (10 mL). The mixture was then heated to reflux (100° C.) overnight under ambient air. After cooling, the mixture was dried under vacuum then redissolved in methylene chloride (100 ml). Solution was washed with water (100 ml) and brine (50 ml), and dried over sodium sulfate. The crude material was run through a plug of silica (16% ethyl acetate in hexanes), and precipitated from methanol to give 564 mg of the material 10 in 49% yield.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureAfter cooling
  3. customthe mixture was dried under vacuum
  4. dissolutionthen redissolved in methylene chloride (100 ml)
  5. washSolution was washed with water (100 ml) and brine (50 ml)
  6. dry with materialdried over sodium sulfate
  7. customprecipitated from methanol

Sources & evidence

ORD record
ord-f8694587c03549e4847b8039044db54d
Source dataset
uspto-grants-2015_06
Patent number
US09051284B2

Reaction notes

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