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

Pyrrole (1.34 g, 20 mmol) was added dropwise, with stirring, to a suspension of sodium hydride (0.48 g, 20 mmol) in dimethyl sulphoxide (20 mL). Once the addition has ended, the resultant brown suspension was stirred for a further 30 min at room temperature before adding carbon disulphide (1.52 g, 20 mmol). The solution was stirred for a further 30 min at room temperature, and finally the benzyl chloride (2.53 g, 20 mmol) was added. After 1 h, water (20 mL) was added to the reaction mixture, followed by diethyl ether (20 mL). The organic phase was separated off, and then the aqueous phase was extracted twice, each time with 20 mL of diethyl ether. The combined organic phases were dried, using magnesium sulphate, and filtered, and the solvent was distilled off. The crude product was separated chromatographically, using 5% strength ethyl acetate in petroleum ether. The pure product was isolated in the form of a yellow oil at 50% yield (2.34 g).

1. additionOnce the addition
2. stirringThe solution was stirred for a further 30 min at room temperature
3. waitAfter 1 h
4. customThe organic phase was separated off
5. extractionthe aqueous phase was extracted twice
6. customThe combined organic phases were dried
7. filtrationfiltered
8. distillationthe solvent was distilled off
9. customThe crude product was separated chromatographically
10. customThe pure product was isolated in the form of a yellow oil at 50% yield (2.34 g)

ORD record

ord-849d854bb8874750bbacd846ebc1dd07

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825193B2