Furfurylamine → HCID 13206466, compound

HRID 1995260Notes

Reaction equation

HRID 1995260 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:15]([C:18]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=2[Cl:41])=[CH:26][C:19]=1[O:20][CH:21]([CH3:25])[C:22](Cl)=[O:23])([O-:17])=[O:16].CCCCCC.C(OCC)(=O)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([NH:7][C:22](=[O:23])[CH:21]([O:20][C:19]1[CH:26]=[C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=2[Cl:41])[CH:28]=[CH:29][C:18]=1[N+:15]([O-:17])=[O:16])[CH3:25])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl ChlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 13206466HCID 13206466, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Furfurylamine (1 gram; 0.01 mole), methylene chloride (50 ml) and triethylamine were charged into a glass reaction vessel equipped with a thermometer, mechanical stirrer and addition funnel. The reaction mixture was cooled to a temperature of -10° C. and 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (4.3 grams; 0.01 mole) dissolved in methylene chloride (50 ml) was added dropwise with stirring and continued cooling. After the addition was completed the reaction mixture was allowed to warm to room temperature with continued stirring over a period of one hour. After this time the reaction mixture was transferred into a separatory funnel and was washed with water (100 ml), with dilute aqueous sodium bicarbonate (100 ml; 5% conc.) and again with water (100 ml). The washed solution was dried by passing it through phase separation paper and was then stripped of solvent leaving a dark red-brown oil. This oil was subjected to chromatography using a 150 cc clay column and hexane/ethyl acetate mixtures with increasing concentrations of ethyl acetate as the eluant. Fractions 9 and 10 were combined and stripped of solvent to yield the desired product N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as an orange solid melting at 128° to 130° C.

Workup

  1. customequipped with a thermometer, mechanical stirrer and addition funnel
  2. additionwas added dropwise
  3. temperaturecontinued cooling
  4. additionAfter the addition
  5. stirringwith continued stirring over a period of one hour
  6. customAfter this time the reaction mixture was transferred into a separatory funnel
  7. washwas washed with water (100 ml), with dilute aqueous sodium bicarbonate (100 ml; 5% conc.) and again with water (100 ml)
  8. customThe washed solution was dried
  9. customthrough phase separation paper
  10. customleaving a dark red-brown oil

Sources & evidence

ORD record
ord-18821e723a984e839e01d84b248aadc0
Source dataset
uspto-grants-1983_09
Patent number
US04404018

Reaction notes

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