Thiophenol → HCID 706762, Verbindung

HRID 2292908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292908
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]#[N:12].[K].[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(S)C=CC=CC=1.[OH-].[K+]>CO.CN(C)C=O>[C:14]1([S:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]#[N:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 855042-Chloro-5-nitrobenzonitrileHCID 68683554Benzenethiol, potassium salt

Produkt 1

HCID 706762HCID 706762, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

4-Chloro-3-cyanonitrobenzene (12.5 g, 6.84 mmol) was added portionwise to a stirred N,N-dimethylformamide (50 mL) solution of thiophenol potassium salt [prepared by adding thiophenol (7.1 mL, 6.9 mmol) to a solution of potassium hydroxide (3.84 g, 6.84 mmol) in methanol followed by removal of the methanol in vacuo]. After stirring at 105° C. for 2.5 hours the mixture was poured into ice-water, filtered, the collected solid washed with water, dissolved in 300 mL of refluxing ethanol (charcoal), filtered, treated with 35 mL of water and refrigerated. The resulting pale yellow solid weighed 13.3 g (76%), mp 82°-84° C. 1H-NMR (250 MHz, CDCl3): 6.93 (d, 1H, J=9.0 Hz, aromatic), 7.51-7.62 (m, 5H, aromatic), 8.12(dd, 1H, J=9.2, 2.5 Hz, aromatic), 8.46 (d, 1H, J=2.5 Hz, aromatic). MS (CI, CH4): 257(M+1).

Aufarbeitung

  1. customprepared
  2. customfollowed by removal of the methanol in vacuo]
  3. additionwas poured into ice-water
  4. filtrationfiltered
  5. washthe collected solid washed with water
  6. dissolutiondissolved in 300 mL of refluxing ethanol (charcoal)
  7. filtrationfiltered
  8. additiontreated with 35 mL of water

Quellen und Nachweise

ORD-Eintrag
ord-191b7394784c4b9b84c46c3767904c41
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684198

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