Triethylamine → HCID 88621057, compound

HRID 235560Notes

Reaction equation

HRID 235560 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15](Cl)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH2:29]([NH:33][C:34]#[N:35])[CH2:30][CH2:31][CH3:32]>C1(C)C=CC=CC=1>[CH2:29]([N:33]([C:34]#[N:35])[C:15](=[O:16])[CH:14]([O:13][C:12]1[CH:19]=[CH:20][C:9]([O:8][C:5]2[C:4]([F:21])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[CH:10][CH:11]=1)[CH3:18])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12295218ButylcyanamideHCID 197926722-[4-(5-Chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride

Product 1

HCID 88621057HCID 88621057, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

While cooling with ice, a solution of 9.9 g (0.030 mole) of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride in 30 ml of toluene is added dropwise to a solution of 3.5 g (0.035 mole) of triethylamine and 3.2 g (0.033 mole) of n-butylcyanamine in 40 m of toluene. After 5 hours, the precipitate is removed by filtration and the filtrate is purified by chromatography through silica gel. The eluate is concentrated by evaporation, affording 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid N-n-butyl-N-cyanamide as a yellowish oil. nD25 : 1.5482.

Workup

  1. temperatureWhile cooling with ice
  2. customthe precipitate is removed by filtration
  3. customthe filtrate is purified by chromatography through silica gel
  4. concentrationThe eluate is concentrated by evaporation

Sources & evidence

ORD record
ord-a349aa3bc68045b3bab8c78b31825d81
Source dataset
uspto-grants-1987_02
Patent number
US04640703

Reaction notes

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