Sodium hydride → 4-Phenyl-1H-pyrrole-3-carbonitrile

A solution of cinnamonitrile (16.53 g) and (para-toluenesulfonyl)methylisocyanide (25 g) in a mixture of ether and dimethyl sulfoxide (450 mL, 2:1) was added dropwise to a stirred suspension of sodium hydride (6.14 g, 60% dispersion in mineral oil) in ether (50 mL). An exothermic reaction took place. The reaction mixture was then stirred at room temperature for 2 hours, then diluted with water (500 mL) and this mixture was extracted three times with ether (250 mL). The combined extracts were washed with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to filter chromatography on a pad of silica eluting with a mixture of ethyl acetate and pentane (1 L, 1:4, v/v) and then with a mixture of ethyl acetate and pentane (2 L, 2:3, v/v). Fractions containing the required material were evaporated and the residue was suspended in pentane (500 mL) with stirring, then filtered to give the title compound as a solid, m.p. 120-122° C. MS: 167 (MH−).

1. customAn exothermic reaction
2. extractionthis mixture was extracted three times with ether (250 mL)
3. washThe combined extracts were washed with brine
4. dry with materialdried over magnesium sulfate
5. customevaporated
6. filtrationto filter chromatography on a pad of silica eluting
7. additionwith a mixture of ethyl acetate and pentane (1 L, 1:4, v/v)
8. additionwith a mixture of ethyl acetate and pentane (2 L, 2:3
9. additionFractions containing the required material
10. customwere evaporated
11. stirringwith stirring
12. filtrationfiltered

ORD record

ord-f0c8c2f7992e448bb37b5702e59a767c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943616B2