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

HRID 1995037Notes

Reaction equation

HRID 1995037 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1)[CH3:2].[CH2:10]([N:12](CC)CC)[CH3:11].[N+:17]([C:20]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[Cl:43])=[CH:28][C:21]=1[O:22][CH:23]([CH3:27])[C:24](Cl)=[O:25])([O-:19])=[O:18]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[CH2:1]([N:3]([CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1)[C:24](=[O:25])[CH:23]([O:22][C:21]1[CH:28]=[C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[Cl:43])[CH:30]=[CH:31][C:20]=1[N+:17]([O-:19])=[O:18])[CH3:27])[CH3:2].[CH2:10]([NH:12][C:24](=[O:25])[C:23]([CH2:4][CH:5]1[O:6][CH2:7][CH2:8][O:9]1)([O:22][C:21]1[CH:28]=[C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[Cl:43])[CH:30]=[CH:31][C:20]=1[N+:17]([O-:19])=[O:18])[CH3:27])[CH3:11]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl ChlorideHCID 13193169N-(1,3-dioxolan-2-yl)methyl ethylamine

Product 2

HCID 20441161N-ethyl-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamideHCID 20441181N-Ethyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

N-Ethyl-N-(1,3-dioxolan-2-ylmethyl)amine (1.31 grams; 0.01 mole), toluene (40 ml) and triethylamine (3 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer, thermometer and addition funnel. A solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (4.2 grams; 0.01 mole) in toluene (30 ml) was added dropwise, with stirring at room temperature. A slight exotherm was observed. After the addition was completed stirring was continued for a period of about 1.5 hours. After this time the reaction mixture was transferred into a separatory funnel and was washed twice with water (60 ml), with dilute aqueous sodium bicarbonate (60 ml; 5% conc.) and again with water (60 ml). The washed organic phase was dried by passing it through phase separation paper and was thereafter stripped of solvent leaving a viscous oil as the residue. This residue was subjected to chromatography using a clay column (150 ml) and mixtures of ethyl acetate and hexane with increasing concentrations of ethyl acetate as the eluant. Nine fractions were collected. Fractions six and seven were combined and stripped of solvents to yield the desired product N-ethyl-(1,3-dioxolan-2-yl-methyl)-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 into a separatory funnel
  6. washwas washed twice with water (60 ml), with dilute aqueous sodium bicarbonate (60 ml; 5% conc.) and again with water (60 ml)
  7. customThe washed organic phase was dried
  8. customthrough phase separation paper
  9. customleaving a viscous oil as the residue
  10. customNine fractions were collected

Sources & evidence

ORD record
ord-d7b635c72a094b58bcd7b788c94474ee
Source dataset
uspto-grants-1983_09
Patent number
US04402729

Reaction notes

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