Phenylhydrazine → 2,2'-bithiophene-5-carboxaldehyde N-phenylhydrazone

HRID 493024

Reaktionsgleichung

Reaktionsgleichung von HRID 493024
[S:1]1[C:5]([CH:6]=O)=[CH:4][CH:3]=[C:2]1[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(O)C>[C:13]1([NH:19][N:20]=[CH:6][C:5]2[S:1][C:2]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)=[CH:3][CH:4]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 7516PhenylhydrazineHCID 364428[2,2'-Bithiophene]-5-carboxaldehyde4×

Produkt 1

HCID 688652442,2'-bithiophene-5-carboxaldehyde N-phenylhydrazone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

A mixture of 2,2′-bithiophene-5-carboxaldehyde (5.0 g, 0.0257 mole, obtained from TCI Europe nv, Boerenveldseweg 6, 2070 Zwijndrecht) and 10 ml of 2-propanol was added to a 100 ml, 2 neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. Heat was applied until all 2,2′-bithiophene-5-carboxaldehyde entered into solution. After all 2,2′-bithiophene-5-carboxaldehyde was dissolved, a hot solution of phenylhydrazine (3.05 g, 2.78 ml, 0.0309 mole, obtained from Aldrich) in 3 ml of 2-propanol was added to the 2,2′-bithiophene-5-carboxaldehyde solution. After the reaction mixture was refluxed for 6 hours, the mixture was cooled to room temperature. The crystals formed were filtered off, and then washed with a mixture of 2-propanol and hexane in 1:1 ratio by volume. The yield of the product, 2,2′-bithiophene-5-carboxaldehyde N-phenylhydrazone, was 6.95 g (94.9%). The product was recrystallized from 2-propanol and dried at 60° C. in a vacuum oven for 6 hours. The melting point of the product was found to be 156-158° C. An infrared absorption spectrum of the product was characterized by the following absorption wave numbers (KBr window, cm−1): 3306 (NH); 3104, 3061 (CHaromatic); 1599 (C═C, C—N). A 1H-NMR spectrum (300 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 7.77 (s, 1H, CH═N); 7.30-7.00 (m, 9H, Ph, Ht, NH); 6.95 (d, 1H, Ht); 6.87 (t, 1H, 4-H Ph). An elemental analysis yielded the following results in weight percent: C, 63.50; H, 4.16; N, 9.97, which compares with the following calculated elemental weight percent for a compound with the formula C15H12N2S2: C, 63.35; H, 4.25; N, 9.85.

Aufarbeitung

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureHeat
  3. temperatureAfter the reaction mixture was refluxed for 6 hours
  4. customThe crystals formed
  5. filtrationwere filtered off
  6. washwashed with a mixture of 2-propanol and hexane in 1:1 ratio by volume
  7. customThe product was recrystallized from 2-propanol
  8. customdried at 60° C. in a vacuum oven for 6 hours
  9. customto be 156-158° C
  10. customAn infrared absorption spectrum of the product
  11. customwas characterized by the following absorption wave numbers (KBr window, cm−1)
  12. customAn elemental analysis yielded the
  13. customfollowing results in weight percent

Quellen und Nachweise

ORD-Eintrag
ord-ceccb4e02f234191b46a6b403a11aac2
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534541B2

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