4-Nitrophenol → HCID 178520521, compound

HRID 744046Notes

Reaction equation

HRID 744046 reaction equation
S(Cl)(Cl)=O.[CH:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([OH:14])[CH:6]=1.[CH:15]1[N:19]=[CH:18][NH:17][C:16]=1/[CH:20]=[CH:21]/[C:22](O)=[O:23].[Cl-].[Cl-].[Ca+2]>>[NH:19]1[CH:15]=[C:16](/[CH:20]=[CH:21]/[C:22]([O:14][C:7]2[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[CH:5][CH:6]=2)=[O:23])[N:17]=[CH:18]1

Participants

5

Reactant 4

HCID 9804-NitrophenolHCID 24386Thionyl ChlorideHCID 736715trans-Urocanic acidHCID 5284359Calcium Chloride

Product 1

HCID 178520521HCID 178520521, compound

Procedure

2 ml (27.5 mmol) of freshly distilled thionyl chloride are added to a finely ground mixture of 1.51 g (10.8 mmol) of p-nitrophenol and 1.5 g (10.8 mmol) of trans-urocanic acid in a round-bottomed flask equipped with a drying tube containing CaCl2. The mixture is progressively brought to 140° C. After 4 h, the mixture is slowly cooled to room temperature. A brown powder is extracted with CHCl3 /MeOH (150 ml, 2:1) while heating. The undissolved material is separated by filtration and the filtrate is treated with active charcoal. Concentration is carried out under vacuum and diethyl ether is added so as to induce precipitation of a solid (1.96 g; overall crude yield: 61%). The latter is recrystallized from MeOH and the product is washed with diethyl ether in order to remove any trace of p-nitrophenol, giving a crystalline white solid, M.p. 220°-222° C.

Workup

  1. customequipped with a drying tube
  2. customis progressively brought to 140° C
  3. extractionA brown powder is extracted with CHCl3 /MeOH (150 ml, 2:1)
  4. temperaturewhile heating
  5. customThe undissolved material is separated by filtration
  6. additionthe filtrate is treated with active charcoal
  7. concentrationConcentration
  8. additionis added so as
  9. customprecipitation of a solid (1.96 g; overall crude yield: 61%)
  10. customThe latter is recrystallized from MeOH
  11. washthe product is washed with diethyl ether in order
  12. customto remove any trace of p-nitrophenol
  13. customgiving a crystalline white solid, M.p. 220°-222° C.

Sources & evidence

ORD record
ord-b775f17883c3412c95788424a6af3124
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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