Triethylamine → HCID 15617221, compound

HRID 622941Notes

Reaction equation

HRID 622941 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.Cl.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14].C(N(CC)CC)C>C(O)C>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1)[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 15617221HCID 15617221, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 2,6-dichloro-3-nitropyridine (1.0 g, 0.00518 mole) and glycine ethyl ester hydrochloride (0.725 g, 0.00518 mole) in absolute ethanol (10 ml) was added triethylamine (1.05 g, 0.0104 mole). The resulting solution was stirred overnight at room temperature under nitrogen. An additional portion of absolute ethanol (10 ml) was added and the suspension was filtered and the solid was washed with 3-10 ml portions of absolute ethanol. The combined filtrate and washings were evaporated under reduced pressure at room temperature to give a yellow solid which was triturated in water (30 ml) collected by filtration, and rinsed with additional water. The solid was recrystallized from isopropyl ether/light petroleum ether, and the resulting solid was purified by column chromatography (10 g of silica gel) with 1:1 isopropyl ether/light petroleum ether as the eluting solvent. The appropriate fraction was recrystallized from isopropyl ether and dried under high vacuum to give the title compound, mp 77.5°-80° C.

Workup

  1. filtrationthe suspension was filtered
  2. washthe solid was washed with 3-10 ml portions of absolute ethanol
  3. customThe combined filtrate and washings were evaporated under reduced pressure at room temperature
  4. customto give a yellow solid which
  5. customwas triturated in water (30 ml)
  6. filtrationcollected by filtration
  7. washrinsed with additional water
  8. customThe solid was recrystallized from isopropyl ether/light petroleum ether
  9. customthe resulting solid was purified by column chromatography (10 g of silica gel) with 1:1 isopropyl ether/light petroleum ether as the eluting solvent
  10. customThe appropriate fraction was recrystallized from isopropyl ether
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-41fa5d708d8943bbabd61e151ac7dfa5
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

Loading…