Pyridine → N-{3-Chloro-4-[(6-chloropyridin-2-yl)oxy]phenyl}propanamide

HRID 437276Notes

Reaction equation

HRID 437276 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[Cl:16])[CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19].N1C=CC=CC=1>O>[Cl:16][C:10]1[CH:11]=[C:12]([NH:15][C:17](=[O:20])[CH2:18][CH3:19])[CH:13]=[CH:14][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 213915003-Chloro-4-[(6-chloropyridin-2-yl)oxy]aniline

Product 1

HCID 21391482N-{3-Chloro-4-[(6-chloropyridin-2-yl)oxy]phenyl}propanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-((6-Chloro-2-pyridinyl)oxy)-3-chlorobenzeneamine (7.1 grams; .028 mole) and propionyl chloride (2.6 grams; .028 mole) were contacted in the presence of 40 ml. of dry pyridine and the resulting reaction mixture allowed to stand at ambient temperatures for a period of about 18 hours. The reaction mixture was then poured into 250 ml. of cold water and allowed to stand for about 15 minutes. The resulting product precipitate was recovered by filtration and taken up in boiling benzene and the resulting solution dried, treated with Norite and filtered. Hexane was then added to the filtrate which was then cooled to precipitate the desired N-(3-chloro-4-((6-chloro-2-pyridinyl)oxy)phenyl)propionamide compound as a white crystalline solid having a melting point of 166°-168° C. The product was found to have carbon, hydrogen, nitrogen and chlorine contents of 55.0, 3.9, 9.0 and 22.5, respectively, as compared with the theoretical contents of 54.0, 3.9, 9.0 and 22.8, respectively, calculated for the named structure.

Workup

  1. additionThe reaction mixture was then poured into 250 ml
  2. waitto stand for about 15 minutes
  3. filtrationThe resulting product precipitate was recovered by filtration
  4. customthe resulting solution dried
  5. additiontreated with Norite
  6. filtrationfiltered
  7. additionHexane was then added to the filtrate which
  8. temperaturewas then cooled
  9. customto precipitate the desired N-(3-chloro-4-((6-chloro-2-pyridinyl)oxy)phenyl)propionamide compound as a white crystalline solid

Sources & evidence

ORD record
ord-588a40fb4fd84806969ee9fc78f2a1ec
Source dataset
uspto-grants-1977_06
Patent number
US04030910

Reaction notes

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