N-[(Furan-2-yl)methyl]butan-1-amine → HCID 20488080, compound

HRID 1995263Notes

Reaction equation

HRID 1995263 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[O:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].[Br:12][C:13]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=2[C:33]#[N:34])=[CH:21][C:14]=1[O:15][CH:16]([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl>[CH2:1]([N:5]([CH2:6][C:7]1[O:11][CH:10]=[CH:9][CH:8]=1)[C:17](=[O:18])[CH:16]([O:15][C:14]1[CH:21]=[C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=2[C:33]#[N:34])[CH:23]=[CH:24][C:13]=1[Br:12])[CH3:20])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 263174N-[(Furan-2-yl)methyl]butan-1-amineHCID 204880712-[2-Bromo-5-(4-bromo-2-cyanophenoxy)phenoxy]propanoyl chloride

Product 1

HCID 20488080HCID 20488080, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

N-Butyl-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-bromo-5-(2-cyano-4-bromophenoxy)phenoxy]propionyl chloride (0.01 mole) in methylene chloride (50 ml) is added dropwise with 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-butyl-N-furfuryl-2-[2-bromo-5-(2-cyano-4-bromophenoxy)phenoxy]propionamide.

Workup

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

Sources & evidence

ORD record
ord-60234c68a40d465ba8166a45e4f9f0c0
Source dataset
uspto-grants-1983_09
Patent number
US04404018

Reaction notes

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