Hydrochloric Acid → HCID 22629926, compound

HRID 1633554Notes

Reaction equation

HRID 1633554 reaction equation
[H-].[Na+].C1(C(C2C=CC=CC=2)=[N:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])C=CC=CC=1.Cl[C:24]1[C:29]([Cl:30])=[CH:28][C:27]([Cl:31])=[CH:26][N:25]=1.Cl>CN(C)C=O>[Cl:30][C:29]1[C:24]([CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH2:10])=[N:25][CH:26]=[C:27]([Cl:31])[CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27666Pyridine, 2,3,5-trichloro-HCID 319508Ethyl 2-(diphenylmethyleneamino)acetate

Product 1

HCID 22629926HCID 22629926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of sodium hydride (0.445 g) in dry dimethylformamide (4 ml) at 0° C. was added ethyl N-(diphenylmethylene)glycinate (1.485 g) in dry dimethylformamide (3 ml) and stirring was continued for 20 minutes. 2,3,5-Trichloropyridine (1.58 g) in dry dimethylformamide (4 ml) was then added dropwise over 10 mins at 5° C. and the reaction mixture was stirred for 2 hours at room temperature. 2M hydrochloric acid (25 ml) was added and stirring continued for 2 hours. The solution was washed with diethyl ether and the layers were separated. The aqueous phase was neutralised with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine (×2), dried (MgSO4), filtered and the solvent removed to leave a residue which was purified by silica gel chromatography eluting with ethyl acetate/light petroleum (40-60° C.) to give the title product.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. stirringstirring
  3. waitcontinued for 2 hours
  4. washThe solution was washed with diethyl ether
  5. customthe layers were separated
  6. extractionextracted with ethyl acetate
  7. washThe combined ethyl acetate layers were washed with brine (×2)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed
  11. customto leave a residue which
  12. customwas purified by silica gel chromatography
  13. washeluting with ethyl acetate/light petroleum (40-60° C.)

Sources & evidence

ORD record
ord-4ea9894506d14ae087824a11e697163f
Source dataset
uspto-grants-2003_01
Patent number
US06503933B1

Reaction notes

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