Triethylamine → HCID 15172320, compound

HRID 1195602Notes

Reaction equation

HRID 1195602 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:4]([O:9][NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH2:18]([N:21]=[C:22]=[O:23])[CH2:19][CH3:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:17][C:2]([F:1])([F:16])[C:3]1[C:4]([O:9][N:10]([C:11]([O:12][CH2:13][CH3:14])=[O:15])[C:22](=[O:23])[NH:21][CH2:18][CH2:19][CH3:20])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 14391372HCID 14391372, compound

Product 1

HCID 15172320HCID 15172320, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

Ethyl N-(3-trifluoromethyl-2-pyridyloxy)-carbamate (2.30 g; 9.19 mmoles) was dissolved in 50 ml of toluene, and 2.34 g (27.6 mmoles) of n-propyl isocyanate and 0.2 g (2.0 mmoles) of triethylamine were added, and the mixture was stirred at 45° C. for 40 hours. The toluene and the excess of n-propyl isocyanate in the reaction mixture were evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane) to give 2.61 g (yield 85 %) of the desired compound as a colorless liquid.

Workup

  1. customThe toluene and the excess of n-propyl isocyanate in the reaction mixture were evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8a116b661be34963a5b56af5e420453e
Source dataset
uspto-grants-1992_05
Patent number
US05112385

Reaction notes

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