Potassium Iodide → HCID 19978914, compound

HRID 1461629Notes

Reaction equation

HRID 1461629 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:19])[CH:11](Cl)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:22]([NH2:24])[CH3:23].[I-].[K+]>CCCCCC.C(OCC)(=O)C>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:19])[CH:11]([NH:24][CH2:22][CH3:23])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6341EthylamineHCID 5079533140690-80-8

Product 1

HCID 19978914HCID 19978914, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

An ethanolic (200 mL) solution of N-(3-trifluoromethylphenyl)-2-chloro-2-phenylacetamide (200.0 grams, 0.06 mol) and 70% aqueous ethylamine (75 mL, excess) and potassium iodide (1.0 gram, catalytic) was stirred at room temperature. The reaction was followed by thin layer chromatography (3:1 hexane-ethyl acetate). The mixture was worked up by removing the ethanol and the excess ethyl amine in a rotary evaporator. The residue was redissolved in fresh ethanol and concentrated hydrochloric acid (excess) was added to convert the product to its hydrochloride salt. Water and other excess reagents were removed by azeotropic distillation in a rotary evaporator. The salt was washed with ethyl ether and dissolved in saturated sodium bicarbonte to regenerate the amine. The product was extracted into ethyl acetate and isolated to give the desired N-(3-trifluoromethylphenyl)-2-ethylamino-2-phenylacetamide (17.1 grams, 89% yield) whose structure was confirmed by nuclear magnetic resonance, infra-red spectroscopy, and mass spectroscopy analysis.

Workup

  1. customby removing the ethanol
  2. customthe excess ethyl amine in a rotary evaporator
  3. dissolutionThe residue was redissolved in fresh ethanol
  4. additionconcentrated hydrochloric acid (excess) was added
  5. customWater and other excess reagents were removed by azeotropic distillation in a rotary evaporator
  6. washThe salt was washed with ethyl ether
  7. dissolutiondissolved in saturated sodium bicarbonte
  8. extractionThe product was extracted into ethyl acetate
  9. customisolated

Sources & evidence

ORD record
ord-7425f4b7115e44c3a4bc5f4e0650c8ea
Source dataset
uspto-grants-1991_12
Patent number
US05076832

Reaction notes

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