Sodium Hydroxide → N,N'-diheptyl-p-xylylenediamine

HRID 1770049Notes

Reaction equation

HRID 1770049 reaction equation
[CH2:1]([NH:8][C:9](=O)[C:10]1[CH:25]=[CH:24][C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].COCCO[Al+]OCCOC.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:17]([NH:16][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4098298N,N'-diheptylterephthalamideHCID 22591236HCID 22591236, compound

Product 1

HCID 14801556N,N'-diheptyl-p-xylylenediamineYield 97.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 3.6 g N,N'-diheptylterephthalamide obtained in Example 1 and 60 ml toluene, was added dropwise 15.6 ml of a 70% solution of bis(2-methoxyethoxy)aluminum hydride in toluene. After heating under reflux for three hours, the reaction mixture was treated with 30 ml of 2.5N aqueous caustic soda solution under ice cooling, and the toluene layer separated was washed with saturated aqueous solution of sodium chloride and dried over a drying agent. Distilling off the solvent from the dried solution gave 3.24 g of N,N'-diheptyl-p-xylylenediamine.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for three hours
  3. customthe toluene layer separated
  4. washwas washed with saturated aqueous solution of sodium chloride
  5. customdried over a drying agent
  6. distillationDistilling off the solvent from the dried solution

Sources & evidence

ORD record
ord-b59ae24b340c4160b73bb2f15813942f
Source dataset
uspto-grants-1995_01
Patent number
US05384425

Reaction notes

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