Triethylamine → HCID 13914798, compound

HRID 2308898Notes

Reaction equation

HRID 2308898 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10].[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH:25][CH2:24][C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[F:21])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 666492-FluorobenzylamineHCID 111624242-(3-Trifluoromethylphenoxy)nicotinoyl chloride

Product 1

HCID 13914798HCID 13914798, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flask were placed 4 grams (g) (0.01326 mole) 2-(3-trifluoromethylphenoxy)nicotinoyl chloride, dissolved in methylene chloride. There was then added 1.7 g (0.01326 mole) of 2-fluorobenzylamine, very slowly, with vigorous stirring. After about 15 minutes, 1.34 g (0.01326 mole) of triethylamine was added dropwise. The reaction mixture was stirred for a short time, then heated intensely for about 5 minutes and allowed to return to room temperature. After approximately 1/2 hour, 5% aqueous sodium carbonate solution was added with stirring continued. The aqueous and organic phases were separated; the aqueous phase was decanted off and the organic phase washed twice with 5% sodium carbonate solution and twice with water. The organic phase was then dried over sodium sulfate; solvent was stripped off, and an oil-like mixture was recovered, which crystallized in a short time. The solid was then washed with pentane to remove any remaining amine. There was obtained 3.5 g (67% of theoretical yield) which was identified as the desired compounds by infrared, nuclear magnetic resonance, and mass spectroscopic analysis.

Workup

  1. customIn a flask were placed
  2. temperatureheated intensely for about 5 minutes
  3. customto return to room temperature
  4. waitAfter approximately 1/2 hour
  5. stirringwith stirring
  6. customThe aqueous and organic phases were separated
  7. customthe aqueous phase was decanted off
  8. washthe organic phase washed twice with 5% sodium carbonate solution and twice with water
  9. dry with materialThe organic phase was then dried over sodium sulfate
  10. customan oil-like mixture was recovered
  11. customwhich crystallized in a short time
  12. washThe solid was then washed with pentane
  13. customto remove any remaining amine
  14. customThere was obtained
  15. custom3.5 g (67% of theoretical yield) which

Sources & evidence

ORD record
ord-763937cacf3c4119b40548ff38f5639c
Source dataset
uspto-grants-1987_09
Patent number
US04692185

Reaction notes

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