Pyridine → HCID 178497632, Verbindung

HRID 1446947

Reaktionsgleichung

Reaktionsgleichung von HRID 1446947
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([O:3][CH3:4])=[O:2].O=S(Cl)Cl.N1C=CC=CC=1.[C:24]([NH:31][NH2:32])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=O>C(COC)OC.C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([N:31]1[C:24](=[O:30])[CH:25]=[CH:26][C:27]([OH:29])=[N:32]1)=[O:9])([O:3][CH3:4])=[O:2]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 20392Monomethyl phthalateHCID 24386Thionyl ChlorideHCID 12898265(Z)-4-hydrazinyl-4-oxobut-2-enoic acid

Produkt 1

HCID 178497632HCID 178497632, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Into a 100 ml round-bottomed flask fitted with a stirrer and reflux condenser there was charged 10.8 g (0.06 mole) of 2-carbomethoxybenzoic acid and 50 ml of chloroform. There was then added 7.8 g (0.066 mole) of SOCl2, followed by refluxing for 2 hr. The chloroform was then removed by distillation, followed by addition of 50 ml. of dimethoxyethane, 4.7 g (0.06 mole) of pyridine and 6.7 g (0.06 mole) of maleic hydrazide. The mixture was allowed to stir over night. The resulting reaction mixture was filtered to remove solids. Then the product was precipitated from the filtrate by addition of water and was recovered as a solid by filtration. The solid material was washed with hexane-ether solvent mixture and was filtered and dried. The yield was 6.6 g, m.p. 144°-145° C. Infrared and nuclear magnetic resonance spectra were consistent with the structure of the compound as named above.

Aufarbeitung

  1. customInto a 100 ml round-bottomed flask fitted with a stirrer
  2. temperaturereflux condenser
  3. temperatureby refluxing for 2 hr
  4. customThe chloroform was then removed by distillation
  5. additionfollowed by addition of 50 ml
  6. customThe resulting reaction mixture
  7. filtrationwas filtered
  8. customto remove solids
  9. customThen the product was precipitated from the filtrate by addition of water
  10. filtrationwas recovered as a solid by filtration
  11. washThe solid material was washed with hexane-ether solvent mixture
  12. filtrationwas filtered
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5397526d64404379a863e61deeb8a066
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04314843

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