Acetyl chloride → HCID 54295898, compound

HRID 977113Notes

Reaction equation

HRID 977113 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:8][CH:7]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][NH:12][C:11]2=[N:16][N+:17]([O-:19])=[O:18])[CH2:6][O:5]1.[C:20](Cl)(=[O:22])[CH3:21]>C(#N)C>[CH3:21][C:20]([N:12]1[CH2:13][CH2:14][CH2:15][N:10]([CH2:9][CH:7]2[CH2:6][O:5][CH:4]([CH3:3])[CH2:8]2)[C:11]1=[N:16][N+:17]([O-:19])=[O:18])=[O:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 136381082HCID 136381082, compound

Product 1

HCID 54295898HCID 54295898, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a suspension of 0.20 g of sodium hydride (60%, oily) in 30 ml of acetonitrile was added a solution of 1.00 g of 1-[(2-methyl-4-tetrahydrofuryl)methyl]-2-(nitroimino) hexahydropyrimidine in 5 ml of acetonitrile at room temperature, followed by stirring for 30 minutes. Next, to the mixture was added a solution of 0.39 g of acetyl chloride in 5 ml of acetonitrile under ice-cooling, and the mixture was then stirred under ice-cooling for 30 minutes and at room temperature for 3 hours. Afterward, insolubles were removed by filtration, and the filtrate was then concentrated under a reduced pressure. The resultant oily substance was purified by silica gel column chromatography (20:1 chloroform/methanol) to obtain 1.15 g of 1-(methylcarbonyl)-3-[(2-methyl-4-tetrahydrofuryl) methyl]-2-(nitroimino)hexahydropyrimidine as a yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was then stirred under ice-
  3. customAfterward, insolubles were removed by filtration
  4. concentrationthe filtrate was then concentrated under a reduced pressure
  5. customThe resultant oily substance was purified by silica gel column chromatography (20:1 chloroform/methanol)

Sources & evidence

ORD record
ord-964cd42cbf6648c39c671389c9876c29
Source dataset
uspto-grants-1997_03
Patent number
US05614527

Reaction notes

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