Diethylamine → N,N-diethyl-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid amide

HRID 1589717Notes

Reaction equation

HRID 1589717 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[F:13][C:14]([F:35])([F:34])[C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:33]=[CH:32][C:25]([O:26][CH:27]([CH3:31])[C:28](Cl)=[O:29])=[CH:24][CH:23]=2)=[N:19][CH:20]=1>C1C=CC=CC=1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:28](=[O:29])[CH:27]([O:26][C:25]1[CH:32]=[CH:33][C:22]([O:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:35])([F:34])[F:13])=[CH:20][N:19]=2)=[CH:23][CH:24]=1)[CH3:31])[CH3:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 8471TriethylamineHCID 130552202-(4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoyl chloride

Product 1

HCID 54279405N,N-diethyl-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid amide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3.4 g (0.046 mol) of diethylamine and 4.8 g (0.47 mol) of triethylamine dissolved in 10 ml of benzene are dropped into the solution of 15.6 g (0.045 mol) of 2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl chloride in 40 ml of anhydrous benzene at 0°-5° C. under stirring. After termination of the portionwise addition, the reaction mixture is stirred for additional 2 hours whilst it is allowed to warm to room temperature. The mixture is filtered off, the precipitate is washed with a little volume of ether, the filtrate is washed first with 5% hydrochloric acid and then with saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and finally evaporated to dryness. The crude product is purified by chromatography on a column filled with silica gel of 0.063-0.2 mm particle size by using a 4:1 mixture of n-hexane/acetone for elution.

Workup

  1. additionAfter termination of the portionwise addition
  2. stirringthe reaction mixture is stirred for additional 2 hours whilst it
  3. filtrationThe mixture is filtered off
  4. washthe precipitate is washed with a little volume of ether
  5. washthe filtrate is washed first with 5% hydrochloric acid
  6. dry with materialwith saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
  7. customfinally evaporated to dryness
  8. customThe crude product is purified by chromatography on a column
  9. additionfilled with silica gel of 0.063-0.2 mm particle size
  10. additiona 4:1 mixture of n-hexane/acetone
  11. washfor elution

Sources & evidence

ORD record
ord-ff56c5794e16498c8cf7e47adfa61959
Source dataset
uspto-grants-1993_04
Patent number
US05199970

Reaction notes

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