Picric Acid → HCID 21271757, compound

HRID 1980345Notes

Reaction equation

HRID 1980345 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][C:19]([CH:21]=[CH2:22])=[CH:20][C:14]2=[N:13]1)(=O)C.C(=O)([O-])O.[Na+].C1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O>CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][C:19]([CH:21]=[CH2:22])=[CH:20][C:14]2=[N:13]1

Participants

5

Reactant 3

HCID 6954Picric AcidHCID 516892Sodium BicarbonateHCID 20402786HCID 20402786, compound

Product 1

HCID 21271757HCID 21271757, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 200 ml flask equipped with a reflux condenser and a mechanical stirrer were placed 2(2-acetoxy-5-methylphenyl)5-vinyl-2H-benzotriazole (7.2 g, 24.5 mmole), a 20% solution of sodium hydrogencarbonate (4.2 g), methanol (110 g) and picric acid (0.01 g). The mixture was heated and kept for 1.5 hours at reflux temperature. The clear, yellow solution was cooled to room temperature, filtered and acidified slowly at 0° to 50° C. with 1N aqueous hydrochloric acid solution. The precipitate was dissolved in chloroform (100 ml), and the organic layer was concentrated. Several precipitations of the chloroform or a dichloromethane solution into methanol were sometimes necessary to remove some insoluble material. The vinyl compound was finally crystallized from methanol/water, dried at 0.05 mm, and gave 3.4 g (55%) yield. Which had the following properties.

Workup

  1. customIn a 200 ml flask equipped with a reflux condenser and a mechanical stirrer
  2. temperatureThe mixture was heated
  3. temperatureat reflux temperature
  4. filtrationfiltered
  5. customacidified slowly at 0° to 50° C. with 1N aqueous hydrochloric acid solution
  6. dissolutionThe precipitate was dissolved in chloroform (100 ml)
  7. concentrationthe organic layer was concentrated
  8. customSeveral precipitations of the chloroform
  9. customto remove some insoluble material
  10. customThe vinyl compound was finally crystallized from methanol/water
  11. customdried at 0.05 mm
  12. customgave 3.4 g (55%)
  13. customyield

Sources & evidence

ORD record
ord-1a00de35f8e540d38b73c1926395fd36
Source dataset
uspto-grants-1985_04
Patent number
US04508882

Reaction notes

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