N-Methylfurfurylamine → N-methyl-N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

HRID 1995261Notes

Reaction equation

HRID 1995261 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[O:8][CH:7]=[CH:6][CH:5]=1.[N+:9]([C:12]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])=[CH:20][C:13]=1[O:14][CH:15]([CH3:19])[C:16](Cl)=[O:17])([O-:11])=[O:10]>C(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[O:8][CH:7]=[CH:6][CH:5]=1)[C:16](=[O:17])[CH:15]([O:14][C:13]1[CH:20]=[C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])[CH:22]=[CH:23][C:12]=1[N+:9]([O-:11])=[O:10])[CH3:19]

Participants

4

Reactant 2

HCID 78492N-MethylfurfurylamineHCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl Chloride

Product 1

HCID 20488072N-methyl-N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

N-Methyl-N-furfurylamine (0.015 mole) triethylamine (5 ml) and methylene chloride (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The reaction mixture is cooled to about -15° C. and a solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (0.01 mole) in methylene chloride (50 ml) is added dropwise with stirring. After the addition is completed the reaction mixture is allowed to warm to room temperature with continued stirring. After this time the mixture is transferred to a separatory funnel and is washed with water and dilute aqueous sodium bicarbonate. The washed solution is then dried, filtered and stripped of solvent leaving a residue. This residue is then purified by subjecting it to elution chromatography using mixtures of ethyl acetate and hexane with increasing concentrations of ethyl acetate as the eluant. The desired fractions determined by IR spectroscopy are then stripped of solvent to yield the desired product N-methyl-N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide.

Workup

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. additionAfter the addition
  4. temperatureto warm to room temperature with continued stirring
  5. customAfter this time the mixture is transferred to a separatory funnel
  6. washis washed with water and dilute aqueous sodium bicarbonate
  7. customThe washed solution is then dried
  8. filtrationfiltered
  9. customleaving a residue
  10. customThis residue is then purified
  11. washto elution chromatography
  12. temperaturewith increasing concentrations of ethyl acetate as the eluant

Sources & evidence

ORD record
ord-d631dccd470d45ce9a17a39db4850dfc
Source dataset
uspto-grants-1983_09
Patent number
US04404018

Reaction notes

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