Sulfuric Acid → 5-(4-Chlorophenyl-phenylmethyl)-2-pyridone

HRID 1390328

Reaktionsgleichung

Reaktionsgleichung von HRID 1390328
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.S(=O)(=O)(O)O.C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:20]2[CH:21]=[CH:22][C:17](=[O:16])[NH:18][CH:19]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 84014-ChlorobenzhydrolHCID 8857Ethyl AcetateHCID 178516071HCID 178516071, Verbindung

Produkt 1

HCID 227487995-(4-Chlorophenyl-phenylmethyl)-2-pyridone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Combine 109.3 g. (0.5 mole) of 4-chlorobenzhydrol with 142.7 g. (1.5 mole) of 2-hydroxypyridine and heat at 150° C. with stirring until molten. Add about 2 ml. of concentrated sulfuric acid and continue heating to 240°-250° C. while removing water from the reaction mixture. Permit the reaction to continue for about 2 hours, then cool the reaction mixture to about 25° C. Treat the resulting solid with ethyl acetate and water and filter to remove the undesired 3-(4-chlorophenyl-phenylmethyl)-2-pyridone. The organic layer is separated and washed with water several times and dried over potassium carbonate and filtered. Concentrate the filtrate to half volume and filter to remove the remaining 3-substituted-2-pyridone. Evaporate the filtrate and dissolve the residue in ethyl ether. Upon standing overnight the 5-(4-chlorophenyl-phenylmethyl)-2-pyridone crystallizes, yield 60 g., m.p. 164°-169° C.

Aufarbeitung

  1. additionAdd about 2 ml
  2. customwhile removing water from the reaction mixture
  3. customthe reaction
  4. filtrationfilter
  5. customto remove the undesired 3-(4-chlorophenyl-phenylmethyl)-2-pyridone
  6. customThe organic layer is separated
  7. washwashed with water several times
  8. dry with materialdried over potassium carbonate
  9. filtrationfiltered
  10. concentrationConcentrate the filtrate to half volume
  11. filtrationfilter
  12. customto remove the remaining 3-substituted-2-pyridone
  13. customEvaporate the filtrate
  14. dissolutiondissolve the residue in ethyl ether
  15. waitUpon standing overnight
  16. customthe 5-(4-chlorophenyl-phenylmethyl)-2-pyridone crystallizes

Quellen und Nachweise

ORD-Eintrag
ord-072bd13939bc4688af71208be225f59c
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138488

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