Water → HCID 56993545, compound

HRID 2290189Notes

Reaction equation

HRID 2290189 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[C:9]12[C:18](=[O:19])O[C:15](=[O:16])[C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14]2.[OH2:20]>C1(C)C=CC=CC=1>[C:15]1(=[O:16])[N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]2[C:18](=[O:19])[C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:15]2=[O:16])[C:18](=[O:20])[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 16402Hexamethylenediamine

Product 1

HCID 56993545HCID 56993545, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

23.2 g (0.2 mole) of 1,6-diaminohexane and 60.8 g (0.4 mole) of 1-cyclohexene-1,2-dicarboxylic anhydride are dissolved in 350 ml of toluene, and the water formed is separated off under reflux in the course of 20 hours. 300 ml of toluene are then distilled off, and the precipitated product is filtered off, washed with toluene/cyclohexane and recrystallised from 600 ml of methanol. The resulting white crystalline proudct is dried at 60° C. in vacuo in the course of 24 hours, affording 50 g (64.1% of theory) of N,N'-hexamethylenebis-3,4,5,6-tetrahydrophthalimide; melting point 123°-124° C. Elemental analysis:

Workup

  1. customis separated off
  2. temperatureunder reflux in the course of 20 hours
  3. distillation300 ml of toluene are then distilled off
  4. filtrationthe precipitated product is filtered off
  5. washwashed with toluene/cyclohexane
  6. customrecrystallised from 600 ml of methanol
  7. customThe resulting white crystalline proudct is dried at 60° C. in vacuo in the course of 24 hours

Sources & evidence

ORD record
ord-47d2b86078f2407582f492c443406721
Source dataset
uspto-grants-1986_10
Patent number
US04615968

Reaction notes

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