Water → HCID 59439661, compound

HRID 391497Notes

Reaction equation

HRID 391497 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=O.[C:11]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.O>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]=2)[CH:7]=[C:8]([Br:10])[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 68297N-Phenyl-o-phenylenediamineHCID 6220773,5-DibromobenzaldehydeHCID 178418268HCID 178418268, compound

Product 1

HCID 59439661HCID 59439661, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 g (75.8 mmol) of 3,5-dibromobenzaldehyde and 16.8 g (90.9 mmol) of N-phenyl-o-phenylenediamine were dissolved in 150 mL of acetic acid. The solution was agitated at room temperature for 30 minutes. Next, 37 g (83.4 mmol) of lead (IV) acetate was added thereto. The resulting product was agitated at 50° C. for 1 hour. Then, water was poured into the acquired reactant. The resulting product was treated with ethyl acetate to perform extraction and the solvent was removed under reduced pressure. The extract was separated through a column and dried, gaining 9.5 g (Y=29%) of a yellow solid.

Workup

  1. stirringThe resulting product was agitated at 50° C. for 1 hour
  2. extractionextraction
  3. customthe solvent was removed under reduced pressure
  4. customThe extract was separated through a column
  5. customdried

Sources & evidence

ORD record
ord-12f6305461cb4020a298254a94713deb
Source dataset
uspto-grants-2013_02
Patent number
US08383932B2

Reaction notes

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