Ethyl isothiocyanate → (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide

HRID 444703Notes

Reaction equation

HRID 444703 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:12][CH:13]2[CH2:15][CH:14]2[CH2:16][CH3:17])=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:20]([N:22]=[C:23]=[S:24])[CH3:21]>CN(C)C=O>[Cl:1][C:2]1[C:7](/[C:8](/[NH:12][CH:13]2[CH2:15][CH:14]2[CH2:16][CH3:17])=[C:9](\[C:10]#[N:11])/[C:23](=[S:24])[NH:22][CH2:20][CH3:21])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10966Ethyl isothiocyanateHCID 24758Sodium hydrideHCID 767595953-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile

Product 1

HCID 58319378(2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamideYield 29.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.15 g, 0.606 mmol, 1 eq.) in 2 ml of dimethyl formamide (DMF) was treated with NaH (60% in mineral oil, 0.029 g, 0.727 mmol, 1.2 eq.) and stirring allowed for 1 h. ethylisothiocyanate (0.105 g, 1.21 mmol, 2 eq.) was added and stirring continued overnight. The reaction was quenched with water and extracted with AcOEt. The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide (0.059 g, 27% yield) as a white solid.

Workup

  1. stirringstirring continued overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with AcOEt
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-56cba9f2574e463ea54be08f4a4fb597
Source dataset
uspto-grants-2013_07
Patent number
US08476197B2

Reaction notes

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