Water → HCID 19087511, compound

HRID 1464248Notes

Reaction equation

HRID 1464248 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:10]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:23][CH2:24][CH2:25][CH3:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][CH2:8][CH3:9].[C:33]([O-:36])(=O)C.[Na+].O.CN(C)[CH:41]=[O:42]>C(OCC)(=O)C>[CH2:6]([N:10]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[O:36])=[CH:29][CH:28]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:23][CH2:24][CH2:25][CH3:26])[C:17]1[CH:22]=[CH:21][C:20]([CH:41]=[O:42])=[CH:19][CH:18]=1)[CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 19753738HCID 19753738, compound

Product 1

HCID 19087511HCID 19087511, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While cooled and stirred, 5.4 g of phosphorus oxychloride were added dropwise to 11.0 g of dimethylformamide, and 3.7 g of N,N'-di-n-butyl-N,N'-diphenyl-1, 5-diaminopentane dissolved in dimethylformamide were added dropwise to the resulting solution, followed by heating and stirring at 85° C. for 2.5 hours. After the completion of the reaction, sodium acetate, water and ethyl acetate were added to the reaction solution to separate an ethyl acetate layer, which was in turn concentrated. The concentrate was purified through a column with a mixed solvent of ethyl acetate with n-hexane to obtain 3.8 g of N,N'-di-n-butyl-N,N'-bis-(4-formylphenyl)-1,5-diaminopentane in a 90% yield (which was found to have a melting point 51°-52° C.).

Workup

  1. temperatureWhile cooled
  2. additionwere added dropwise to the resulting solution
  3. temperatureby heating
  4. stirringstirring at 85° C. for 2.5 hours
  5. additionwere added to the reaction solution
  6. customto separate an ethyl acetate layer, which
  7. concentrationconcentrated
  8. customThe concentrate was purified through a column with a mixed solvent of ethyl acetate with n-hexane

Sources & evidence

ORD record
ord-f9e686a5943e4e4e930e30eeb85d8603
Source dataset
uspto-grants-1994_04
Patent number
US05304528

Reaction notes

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