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Triethylamine → 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid N-n-butyl-N-cyanamide

HRID 845705
Notes
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Reaction equation

HRID 845705 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 886210572-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid N-n-butyl-N-cyanamide

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 filtrate 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 filtrate
  3. customthe filtrate is purified by chromatography through silica gel
  4. concentrationThe eluate is concentrated by evaporation

Sources & evidence

ORD record
ord-cfcb77748a154b4b8cc759f0b1a434dc
Source dataset
uspto-grants-1988_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04759796

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes