Triethylamine → HCID 18536460, compound

HRID 412542Notes

Reaction equation

HRID 412542 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Cl.[C:14]([O:18][C:19](=[O:22])[CH2:20][NH2:21])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>C(O)C>[C:14]([O:18][C:19](=[O:22])[CH2:20][NH:21][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 18536460HCID 18536460, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzonitrile (33.87 g) and glycine tert-butyl ester hydrochloride (55.98 g) in ethanol (400 ml) was added triethylamine (77.6 ml), and the mixture was stirred at room temperature for 15 hours and then at 50° C. for 3 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was extracted with ethyl acetate. The extract was washed with 10% aqueous citric acid solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was washed with diisopropyl ether and collected by filtration to give the title compound (38.419 g).

Workup

  1. waitat 50° C. for 3 hours
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. extractionthe obtained residue was extracted with ethyl acetate
  5. washThe extract was washed with 10% aqueous citric acid solution and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. washThe obtained residue was washed with diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7d5568cbb03f4f579f10be763ac93b89
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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