Chloroacetonitrile → 3-Cyanomethyl-2,3-dihydro-4-methyl-2-oxo-1-pyrid-3-ylmethyleneamino-1H-imidazole

HRID 1489511Notes

Reaction equation

HRID 1489511 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6](=[O:17])[N:7]([N:9]=[CH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=1.Cl[CH2:19][C:20]#[N:21]>CN(C)C=O>[C:20]([CH2:19][N:5]1[C:4]([CH3:3])=[CH:8][N:7]([N:9]=[CH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:6]1=[O:17])#[N:21]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 541240302,3-Dihydro4-methyl-2-oxo-1-pyrid-3-ylmethyleneamino-1H-imidazole

Product 1

HCID 867514133-Cyanomethyl-2,3-dihydro-4-methyl-2-oxo-1-pyrid-3-ylmethyleneamino-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.72 g of sodium hydride are added to a suspension of 4.1 g of 2,3-dihydro-4-methyl-2-oxo-1-pyrid-3-ylmethyleneamino-1H-imidazole in 80 ml of N,N-dimethylformamide. The mixture is heated to 50°, treated with a solution of 1.89 g of chloroacetonitrile in 20 ml of N,N-dimethylformamide, and stirred for 30 minutes. The N,N-dimethylformamide is then removed on a rotary evaporator. In a mixer, the residue is mixed intimately with water. The crystals are filtered off, yielding the title compound melting at 195°-198°.

Workup

  1. temperatureThe mixture is heated to 50°
  2. customThe N,N-dimethylformamide is then removed on a rotary evaporator
  3. additionIn a mixer, the residue is mixed intimately with water
  4. filtrationThe crystals are filtered off

Sources & evidence

ORD record
ord-7d31497fca674e108d78873ec29a352a
Source dataset
uspto-grants-1997_10
Patent number
US05679623

Reaction notes

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