Sodium Iodide → HCID 22355248, compound

HRID 1647843Notes

Reaction equation

HRID 1647843 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH:6]1[CH2:10][CH2:9][O:8][CH2:7]1)(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:26]([NH2:29])[CH2:27][CH3:28]>C(O)C>[O:8]1[CH2:9][CH2:10][CH:6]([CH2:5][NH:29][CH2:26][CH2:27][CH3:28])[CH2:7]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7852PropylamineHCID 11430Potassium CarbonateHCID 15335290Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl ester

Product 1

HCID 22355248HCID 22355248, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 3.00 g of (tetrahydro-3-furanyl)methyl tosylate, 0.20 g of sodium iodide, 3.50 g of potassium carbonate, 4.00 g of propylamine and 30 ml of ethanol was refluxed for 8 hours. After separation of insoluble matters by filtration, the reaction fluid was concentrated under a reduced pressure to obtain crude N-{(tetrahydro-3-furanyl)methyl}propylamine. To this were added 1.90 g of 1,1-bis(methylthio)-2-nitroethylene and 16 ml of acetonitrile. The resulting mixture was refluxed for 4 hours. The reaction fluid was concentrated under a reduced pressure, and purified by silica gel column chromatograpy (eluent: ethyl acetate/hexane=1/2) to obtain 1.00 g of 1-[N-{(tetrahydro-3-furanyl)methyl}-N-propylamino]-1-methylthio-2-nitroethylene. A mixture comprising 0.25 g of the 1-[N-{(tetrahydro-3-furanyl)methyl}-N-propylamino]-1-methylthio-2-nitroethylene obtained above and 3 ml of 40% methylamine in methanol solution was stirred for 40 minutes at room temperature. The reaction fluid was concentrated under a reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate/methanol=7/1) to obtain 0.22 g of 1-[N-{(tetrahydro-3-furanyl)methyl}propylamino]-1-methylamino-2-nitroethylene.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customAfter separation of insoluble matters
  3. filtrationby filtration
  4. concentrationthe reaction fluid was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-0a3cc9bfdf7c4a0caee1dcf0e90aeda0
Source dataset
uspto-grants-1995_07
Patent number
US05434181

Reaction notes

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