Triethylamine → HCID 13937120, compound

HRID 651906Notes

Reaction equation

HRID 651906 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([Cl:11])([Cl:10])[Cl:9])[CH:5]=[C:4]([OH:12])[N:3]=1.C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[C:21](=[O:22])([O:23][CH2:24][CH3:25])[O:12][C:4]1[CH:5]=[C:6]([C:8]([Cl:10])([Cl:11])[Cl:9])[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178516063HCID 178516063, compound

Product 1

HCID 13937120HCID 13937120, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution was prepared by dissolving 6.17 grams (g) (0.025 mole (m)) of 2-chloro-6-hydroxy-4-(trichloromethyl)pyridine in 100 milliliters of toluene. To this solution was added 2.53 g (0.025 m) of triethylamine. To this mixture was then added 2.71 g (0.025 m) of ethyl chloroformate dissolved in 20 ml of toluene. The mixture was stirred at 50° C. for 4 hours. The salt which formed was removed by filtration and the toluene was removed by evaporation under reduced pressure. Using a short path distillation (Kugelrohr) at 130° C. and 80 millimeters of mercury, 6-chloro-4-(trichloromethyl)-2-pyridinyl ethyl carbonate was obtained in a yield of 6.65 g (83 percent of theory). The product had a refractive index of n(25/d)=1.5354. The structure of the product was confirmed by its NMR spectrum (Compound No. 1).

Workup

  1. customA solution was prepared
  2. customThe salt which formed
  3. customwas removed by filtration
  4. customthe toluene was removed by evaporation under reduced pressure
  5. distillationa short path distillation (Kugelrohr) at 130° C.

Sources & evidence

ORD record
ord-cee8b9f7cf614aaa92f5cf236addfee1
Source dataset
uspto-grants-1987_06
Patent number
US04670045

Reaction notes

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