Sodium hydride → HCID 86745662, compound

HRID 1030251Notes

Reaction equation

[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2([CH3:31])[C:25](=[C:26]=[S:27])[C:24](=[C:28]=[S:29])[CH2:23][CH2:22][C:21]2=O)[CH:15]=1>O1CCCC1.C(OCC)(=O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2([CH3:31])[C:25](=[C:26]=[S:27])[C:24](=[C:28]=[S:29])[CH2:23][CH2:22][C:21]2=[CH:3][C:1]#[N:2])[CH:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of diethyl cyanomethylphosphonate (18.2 g, 0.1 mol) in dry tetrahydrofuran (200 ml) at 25° C. was treated with sodium hydride (4.5 g of a 60% oil dispersion). After 30 mins at 25° C. the mixture was treated with 2-(pyrid-3-yl)-2-methyldithiocarbonylcyclohexanone (24.7 g, 0.93 mol) in dry tetrahydrofuran (100 ml). After 3 hrs at reflux the mixture was cooled to 25° C. over 30 mins, diluted with ethyl acetate (500 ml) and then washed with water (500 ml). The organic phase was removed and dried over magnesium sulphate and then filtered. Concentration in-vacuo (50° C.; 20 mm Hg) afforded a crude oil which wa purified by flash chromatography over silica gel, eluting with ethyl acetate/n-hexane (25:75) to give 2-(pyrid-3-yl)-2-methyldithiocarbonyl-1-cyanomethylenecyclohexane (7.4 g, 0.026 mol) as an orange gum.

Workup

temperatureAfter 3 hrs at reflux the mixture
washwashed with water (500 ml)
customThe organic phase was removed
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationConcentration in-vacuo (50° C.; 20 mm Hg)
customafforded a crude oil which
customwa purified by flash chromatography over silica gel
washeluting with ethyl acetate/n-hexane (25:75)

Sources & evidence

ORD record: ord-484f9dd815144f19909d6026ac3feebe
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104883

Reaction notes

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