Formamide → 4-(Diphenylmethyl)-Picolinamide

HRID 1390332

Reaktionsgleichung

Reaktionsgleichung von HRID 1390332
[CH:1]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]([NH2:22])=[O:21].S(=O)(=O)(O)O.C(OO)(C)(C)C>>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH2:22])=[O:21])[CH:15]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 713FormamideHCID 1118Sulfuric AcidHCID 6410tert-Butyl hydroperoxideHCID 772524-Benzhydrylpyridine

Produkt 1

HCID 227487444-(Diphenylmethyl)-Picolinamide

Versuchsvorschrift

Dissolve 20 g. (0.082 mole) of 4-benzhydrylpyridine in 200 ml. of formamide and, with external cooling, add 4.35 ml. (0.082 mole) of sulfuric acid. Adjust the reaction temperature to 5°-10° C. while adding 21.6 g. (0.24 mole) of t-butyl hydroperoxide and 67 g. (0.24 mole) of ferrous sulfate over a 30 minute interval. Remove the iron salts by filtration. Wash the precipitate with chloroform and water and separate the two liquid phases. Extract the aqueous phase with chloroform, wash the combined chloroform phases with water and dry. Concentrate the extract to a residue, dissolve the residue in ether, filter and obtain the product of this step from the ether solution, yield 3.5 g., m.p. 165°-170° C. Additional product may be obtained by extracting the iron salts with refluxing chloroform.

Aufarbeitung

  1. dissolutionDissolve 20 g
  2. customto 5°-10° C.
  3. additionwhile adding 21.6 g
  4. customRemove the iron salts
  5. filtrationby filtration
  6. washWash the precipitate with chloroform and water
  7. customseparate the two liquid phases
  8. extractionExtract the aqueous phase with chloroform
  9. washwash the combined chloroform phases with water
  10. customdry
  11. concentrationConcentrate the
  12. extractionextract to a residue
  13. dissolutiondissolve the residue in ether
  14. filtrationfilter
  15. customobtain the product of this step from the ether solution, yield 3.5 g
  16. customAdditional product may be obtained
  17. extractionby extracting the iron salts with refluxing chloroform

Quellen und Nachweise

ORD-Eintrag
ord-3e08a716d8004c488a55c82106400101
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138488

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