Ethylenediamine → HCID 13802796, compound

HRID 977119Notes

Reaction equation

HRID 977119 reaction equation
CS(O[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][O:8]1)(=O)=O.[CH2:12]([NH2:15])[CH2:13][NH2:14].C([O-])([O-])=O.[K+].[K+]>[I-].[Na+].C(OCC)(=O)C>[O:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[CH2:6][NH:14][CH2:13][CH2:12][NH2:15]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 266119(Tetrahydrofuran-2-yl)methyl methanesulfonate

Product 1

HCID 13802796HCID 13802796, compound

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.42 g of (tetrahydro-2-furanyl)methyl methanesulfonate, 5 ml of ethylendiamine, 1.53 g of potassium carbonate, anhydrous, and 0.1 g of sodium iodide was stirred at 60° C. for 4 hours. After the completion of reaction, ethyl acetate was added, and insolubles were then removed by filtration. The filtrate was concentrated under a reduced pressure, and the resultant residue was poured into 10 ml of a 6N aqueous solution of sodium hydroxide, followed by extraction with 100 ml of methylene chloride. Next, the extract was dried over sodium sulfate, anhydrous, and then concentrated under a reduced pressure to obtain 1.2 g of N-[(tetrahydro-2-furanyl) methyl]ethylenediamine as a yellow oil.

Workup

  1. additionwas added
  2. custominsolubles were then removed by filtration
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. additionthe resultant residue was poured into 10 ml of a 6N aqueous solution of sodium hydroxide
  5. extractionfollowed by extraction with 100 ml of methylene chloride
  6. dry with materialNext, the extract was dried over sodium sulfate, anhydrous
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-971c122948bd49b687fb6da56fdc54d4
Source dataset
uspto-grants-1997_03
Patent number
US05614527

Reaction notes

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