Sodium hydride → HCID 178430609, compound

HRID 326588Notes

Reaction equation

HRID 326588 reaction equation
[H-].[Na+].[C:3]([N:5]=[C:6]1[NH:10][CH2:9][CH2:8][NH:7]1)#[N:4].Cl[C:12]1[C:17]2[CH:18]=[C:19]([C:22]#[N:23])[CH:20]=[CH:21][C:16]=2[O:15][C:14]([CH3:25])([CH3:24])[N:13]=1>CN(C)C=O>[C:22]([C:19]1[CH:20]=[CH:21][C:16]2[O:15][C:14]([CH3:24])([CH3:25])[N:13]=[C:12]([N:7]3[CH2:8][CH2:9][NH:10][C:6]3=[N:5][C:3]#[N:4])[C:17]=2[CH:18]=1)#[N:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 147215882,2-dimethyl-4-chloro-6-cyano-2H-1,3-benzoxazineHCID 178512073HCID 178512073, compound

Product 1

HCID 178430609HCID 178430609, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.24 g) in dimethylformamide (10 ml) was added 2-cyanoiminoimidazolidine (1.00 g) with ice-cooling and the mixture was stirred at room temperature for 10 minutes. Then, 4-chloro-6-cyano-2,2-dimethyl-2H-1,3-benzoxazine (1.09 g) was added to the mixture and the mixture was stirred at room temperature for additional 5 hours. The reaction mixture was extracted with addition of ethyl acetate and an aqueous sodium bicarbonate solution. The ethyl acetate layer was successively washed with water and aqueous saturated saline solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was crystallized from ether to obtain 6-cyano-4-(2-cyanoimino-imidazoline-1-yl)-2,2-dimethyl-2H-1,3-benzoxazine (0.23 g) (Compound 19).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for additional 5 hours
  3. extractionThe reaction mixture was extracted with addition of ethyl acetate
  4. washThe ethyl acetate layer was successively washed with water and aqueous saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-2419dc4710d64092ba2bbc3658e9ac38
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

Loading…