Acetyl chloride → HCID 54459541, compound

HRID 977111Notes

Reaction equation

HRID 977111 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][NH:9][C:8]2=[N:13][N+:14]([O-:16])=[O:15])[CH2:2]1.[H-].[Na+].[C:19](Cl)(=[O:21])[CH3:20]>C(#N)C>[CH3:20][C:19]([N:9]1[CH2:10][CH2:11][CH2:12][N:7]([CH2:6][CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[C:8]1=[N:13][N+:14]([O-:16])=[O:15])=[O:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 136381081174458-00-5

Product 1

HCID 54459541HCID 54459541, compoundYield 16.9%

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)hexahydropyrimidine, 0.07 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, 0.11 g of acetyl chloride was dropwise added thereto over 10 minutes, and the mixture was then stirred at room temperature for 2 hours. After the completion of reaction, insolubles were removed by filtration, and concentration was then carried out under a reduced pressure. The resultant oily substance was purified by silica gel column chromatography (2:1 ethyl acetate/acetone) to obtain 0.06 g of 1-(methylcarbonyl)-2-(nitroimino)-3-[(tetrahydro-3-furanyl)methyl]hexahydropyrimidine.

Workup

  1. additionwas dropwise added
  2. waitover 10 minutes
  3. stirringthe mixture was then stirred at room temperature for 2 hours
  4. customAfter the completion of reaction, insolubles
  5. customwere removed by filtration, and concentration
  6. customThe resultant oily substance was purified by silica gel column chromatography (2:1 ethyl acetate/acetone)

Sources & evidence

ORD record
ord-826087ba90254fe6a0dd98b38af46862
Source dataset
uspto-grants-1997_03
Patent number
US05614527

Reaction notes

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