Diethyl (ethoxymethylene)malonate → HCID 59718849, compound

HRID 1925622Notes

Reaction equation

HRID 1925622 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>C1(C)C=CC=CC=1>[CH:10]1([CH2:9][N:8]2[C:19](=[O:18])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][C:3]3[CH2:2][S:1][CH2:6][CH2:5][C:4]2=3)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 66173Tetrahydrothiopyran-4-oneHCID 76688Cyclohexanemethylamine

Product 1

HCID 59718849HCID 59718849, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After a toluene (40 mL) solution of tetrahydrothiopyran-4-one (5.05 g, 43.5 mmol) and aminomethylcyclohexane (5.41 g, 47.8 mM) was heated and refluxed under azeotropic dehydration for 4 hours, diethyl ethoxymethylenemalonate (9.40 g, 43.5 mmol) was added, and the mixture was further continued to be heated and refluxed for 17 hours. The solvent was removed by distillation under reduced pressure, and the residue was refined with silica gel (160 g) column chromatography (ethyl acetate-toluene of 1:5 in mixing ratio and then that of 2:3), and red oily ethyl 1-cyclohexylmethyl-2-oxo-1,5,7,8,tetrahydro-2H-thiopyrano[4,3-b]pyridine-3-carboxylate (AA08, 8.17 g, 31.5%) was obtained.

Workup

  1. temperaturerefluxed under azeotropic dehydration for 4 hours
  2. temperatureto be heated
  3. temperaturerefluxed for 17 hours
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionin mixing ratio

Sources & evidence

ORD record
ord-0059131a3ab944d0a00912dc0df640bc
Source dataset
uspto-grants-2012_05
Patent number
US08178681B2

Reaction notes

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