Butyryl chloride → HCID 53803196, compound

HRID 977115Notes

Reaction equation

HRID 977115 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[N:12][N+:13]([O-:15])=[O:14])[CH2:2]1.[H-].[Na+].[C:18](Cl)(=[O:22])[CH2:19][CH2:20][CH3:21]>C(#N)C>[CH2:19]([C:18]([N:9]1[CH2:10][CH2:11][N:7]([CH2:6][CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[C:8]1=[N:12][N+:13]([O-:15])=[O:14])=[O:22])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 24758Sodium hydrideHCID 136133141HCID 136133141, compound

Product 1

HCID 53803196HCID 53803196, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.30 g of 1-[(tetrahydro-3-furanyl)methyl]-2-(nitroimino)imidazolidine, 0.084 g of sodium hydride (60%) and 10 ml of acetonitrile was stirred at 50° C. for 30 minutes. After this mixture was cooled on ice, 0.22 g of n-butanoyl chloride was added dropwise thereto over 30 minutes, and the solution was then stirred at room temperature for 2 hours. After the completion of reaction, insolubles were removed by filtration, and the filtrate was then concentrated under a reduced pressure. The resultant residue was purified by silica gel column chromatography (2:1 ethyl acetate/acetone) to obtain 0.27 g of 1-(propylcarbonyl)-2-(nitroimino)-3-[(tetrahydro-3-furanyl) methyl]imidazolidine.

Workup

  1. additionwas added dropwise
  2. waitover 30 minutes
  3. stirringthe solution was then stirred at room temperature for 2 hours
  4. customAfter the completion of reaction, insolubles
  5. customwere removed by filtration
  6. concentrationthe filtrate was then concentrated under a reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (2:1 ethyl acetate/acetone)

Sources & evidence

ORD record
ord-de883a8f03ec45e4b129a00eba15c405
Source dataset
uspto-grants-1997_03
Patent number
US05614527

Reaction notes

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