Carbon Disulfide → 1H-Pyrrole-1-carbodithioic acid phenylmethyl ester

HRID 479088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479088
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[C:8](=[S:10])=[S:9].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O.C(OCC)C.O>[N:1]1([C:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[S:9])[CH:5]=[CH:4][CH:3]=[CH:2]1

Komponenten

8

Edukt 4

HCID 6348Carbon DisulfideHCID 7503Benzyl ChlorideHCID 8027PyrroleHCID 24758Sodium hydride

Produkt 1

HCID 121494521H-Pyrrole-1-carbodithioic acid phenylmethyl esterAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Pyrrole (1.34 g, 20 mmol) was added dropwise to a stirred suspension of sodium hydride (0.48 g, 20 mmol) in dimethyl sulfoxide (20 mL). On completion of addition the resulting brown solution was stirred at room temperature for 30 minutes before the addition of carbon disulfide (1.52 g, 20 mmol). The solution was allowed to stir at room temperature for a further half hour and benzyl chloride (2.53 g, 20 mmol) added. Water (20 mL) was added after 1 hour followed by diethyl ether (20 mL). The organic layer was separated and the aqueous layer extracted with diethyl ether (2×20 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent removed. The crude product was chromatographed using 5% ethyl acetate in petroleum spirits to isolate the product as a yellow oil (2.34 g, 50%). 1H-nmr (CDCl3) δ 4.60 (2H), 6.30 (2H), 7.40 (5H), 7.70 (2H). 13C-nmr (CDCl3) δ 41.7, 114.2, 120.6, 128.0, 128.8, 129.4, 135.0, 189.0.

Aufarbeitung

  1. additionOn completion of addition the resulting brown solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with diethyl ether (2×20 mL)
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe crude product was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-294312d761c44f96a499b9386e7fd519
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642318B1

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