Water → HCID 59439661, compound

HRID 1621304Notes

Reaction equation

HRID 1621304 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 obtained reactant. The resulting product was treated with ethyl acetate to perform extraction and the solvent was removed under a reduced pressure. The extract was separated through a column and dried, obtaining 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 a reduced pressure
  4. customThe extract was separated through a column
  5. customdried
  6. customobtaining 9.5 g (Y=29%) of a yellow solid

Sources & evidence

ORD record
ord-33fbacba96104733ae9428a27f656587
Source dataset
uspto-grants-2014_07
Patent number
US08772632B2

Reaction notes

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