Maleic Anhydride → HCID 89928437, compound

HRID 2201641Notes

Reaction equation

HRID 2201641 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[CH:10]1>O1CCCC1>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 16402Hexamethylenediamine

Product 1

HCID 89928437HCID 89928437, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, into a reaction vessel were charged 10.00 g (86.1 mmol) of 1,6-diaminohexane and 400 ml of tetrahydrofuran. A solution prepared by dissolving 8.44 g (86.1 mmol) of maleic anhydride in 25 ml of tetrahydrofuran was dropped into this under cooling with ice over a period of 2 hours, then, the mixture was stirred at room temperature overnight. After completion of the reaction, the deposited solid was isolated by filtration, and dried under reduced pressure. The resultant solid was dissolved in 100 ml of methanol, 100 ml of chloroform was added, and the solvent was distilled off under reduced pressure, the resultant solid was dried under reduced pressure at 35° C., to obtain 17 g of (2Z)-4-[(6-aminohexyl)amino]-4-oxo-2-butenoic acid as a white solid. NMR measurement thereof revealed a content of (2Z)-4-[(6-aminohexyl)amino]-4-oxo-2-butenoic acid of 38.4%. Net quantity: 8.1 g, yield: 43.9%.

Workup

  1. customA solution prepared
  2. additionwas dropped into
  3. temperaturethis under cooling with ice over a period of 2 hours
  4. customAfter completion of the reaction
  5. customthe deposited solid was isolated by filtration
  6. customdried under reduced pressure
  7. dissolutionThe resultant solid was dissolved in 100 ml of methanol
  8. addition100 ml of chloroform was added
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe resultant solid was dried under reduced pressure at 35° C.

Sources & evidence

ORD record
ord-7ebac7553def4371b6fd7bff506c9369
Source dataset
uspto-grants-2016_06
Patent number
US09365497B2

Reaction notes

Loading…