Triethylamine → N-propyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

HRID 1995038Notes

Reaction equation

HRID 1995038 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)[CH2:2][CH3:3].C(N(CC)CC)C.[N+:18]([C:21]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=2[Cl:44])=[CH:29][C:22]=1[O:23][CH:24]([CH3:28])[C:25](Cl)=[O:26])([O-:20])=[O:19]>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)[C:25](=[O:26])[CH:24]([O:23][C:22]1[CH:29]=[C:30]([O:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=2[Cl:44])[CH:31]=[CH:32][C:21]=1[N+:18]([O-:20])=[O:19])[CH3:28])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl ChlorideHCID 20441139N-n-propyl-N-(1,3-dioxolan-2-ylmethyl)amine

Product 1

HCID 20441152N-propyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

N-n-Propyl-N-(1,3-dioxolan-2-ylmethyl)amine (1.33 grams; 0.0092 mole), dry toluene (60 ml) and triethylamine (3.0 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer, thermometer and addition funnel. The reaction mixture was blanketed under nitrogen gas and a solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (3.9 grams; 0.0092 mole) in toluene (40 ml) was added dropwise with stirring. A slight exotherm was observed. After the addition was completed stirring was continued at room temperature for a period of about 1.5 hours. After this time the reaction mixture was transferred to a separatory funnel and was washed with water and dilute aqueous sodium bicarbonate. The washed solution was then dried and stripped of solvent leaving a viscous oil as the residue. This residue was then chromatographed through clay using ethyl acetate-hexane mixtures with increasing concentrations of ethyl acetate as the eluant. A total of nine fractions were collected. Fractions 5 and 6 were combined and stripped of solvents to yield the desired product N-propyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as an amber gum.

Workup

  1. customequipped with a magnetic stirrer
  2. additionthermometer and addition funnel
  3. additionAfter the addition
  4. stirringwas completed stirring
  5. customAfter this time the reaction mixture was transferred to a separatory funnel
  6. washwas washed with water and dilute aqueous sodium bicarbonate
  7. customThe washed solution was then dried
  8. customleaving a viscous oil as the residue
  9. customThis residue was then chromatographed through clay
  10. temperaturewith increasing concentrations of ethyl acetate as the eluant
  11. customA total of nine fractions were collected

Sources & evidence

ORD record
ord-ffe6da874bbd437eb1df04f750d65c89
Source dataset
uspto-grants-1983_09
Patent number
US04402729

Reaction notes

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