Triethylamine → HCID 1118253, compound

HRID 1494642Notes

Reaction equation

HRID 1494642 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.C(N(CC)CC)C.[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>CC1C=CC=CC=1>[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 1118253HCID 1118253, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of 28.2 parts of 3-pyridinamine, 59 parts of N,N-diethylethanamine and 450 parts of methylbenzene were added dropwise 39 parts of 4-fluorobenzoyl chloride (exothermic reaction, the temperature rose to 40° C.). Upon complete addition, stirring was continued for 2 hours at reflux temperature. After cooling, the precipitated product was filtered off and dissolved in trichloromethane. The organic layer was washed twice with water, dried, filtered and evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 52.3 parts (80.6%) of 4-fluoro-N-(3-pyridinyl)benzamide; mp. 150.2° C. (int. 66).

Workup

  1. customexothermic reaction
  2. customrose to 40° C.
  3. additionUpon complete addition
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. filtrationthe precipitated product was filtered off
  7. dissolutiondissolved in trichloromethane
  8. washThe organic layer was washed twice with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-b1dfb9ccb6de4550bd97af7f3ce9ac20
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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