1,3-Propanediamine → HCID 20470672, compound

HRID 1388279Notes

Reaction equation

HRID 1388279 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].C(OC(C)C)(C)C.[F:13][C:14]([F:35])([S:31](F)(=[O:33])=[O:32])[C:15]([F:30])([F:29])[C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20]>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][S:31]([C:14]([F:13])([F:35])[C:15]([F:29])([F:30])[C:16]([F:27])([F:28])[C:17]([F:25])([F:26])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])(=[O:33])=[O:32]

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 7914Diisopropyl EtherHCID 679181-Hexanesulfonyl fluoride, 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-

Product 1

HCID 20470672HCID 20470672, compoundYield 99.6%

Conditions

Temperature
50 °C

Procedure

111 g (1.5 moles) of 1,3-diaminopropane and 300 g of fully dehydrated isopropyl ether were weighed in an atmosphere of nitrogen into a 2-liter three-necked round-bottomed flask equipped with a cooling condenser and stirrer. With sufficient stirring, 237 g (0.59 mole) of perfluorohexyl sulfonyl fluoride was added dropwise at room temperature from a dropping funnel. The mixture was stirred at 50° C. for 3 hours, and then the isopropyl ether was removed under reduced pressure. The oily residue was dissolved in 200 ml of ethanol, and gradually poured into 5 liters of distilled water with stirring. The resulting crystals were aged. The supernatant liquid was removed by decantation, and 1 liter of 0.5 N aqueous sodium hydroxide solution was added to wash the crystals. Decantation was performed for three more times using 5 liters of distilled water each time. The crystals were collected by filtration, washed with distilled water and dried at 60° C. under reduced pressure. There was obtained 268 g of N-(3 -aminopropyl)perfluorohexyl sulfonamide having a sufficient purity for use in the subsequent reaction.

Workup

  1. customequipped with a cooling condenser and stirrer
  2. customthe isopropyl ether was removed under reduced pressure
  3. dissolutionThe oily residue was dissolved in 200 ml of ethanol
  4. additiongradually poured into 5 liters of distilled water
  5. stirringwith stirring
  6. customThe supernatant liquid was removed by decantation, and 1 liter of 0.5 N aqueous sodium hydroxide solution
  7. additionwas added
  8. washto wash the crystals
  9. filtrationThe crystals were collected by filtration
  10. washwashed with distilled water
  11. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-88bd85b9fd5c4b5e905369d3e3cf8549
Source dataset
uspto-grants-1984_02
Patent number
US04431595

Reaction notes

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