Reaction #44019

ord-916c1a439c9a48dfb8e5e3b3454c7fcd

Reaction equation

CCOC(=O)C1CC(=O)C=CN1S(=O)(=O)c1ccc(Cl)cc1
Compound 103
CCOC(=O)C1CC(=O)C=CN1S(=O)(=O)c1ccc(Cl)cc1
ethyl 1-(4-chlorophenylsulfonyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate
COC(OC)N(C)C
DMF-DMA
→
CCOC(=O)C1C(=CN(C)C)C(=O)C=CN1S(=O)(=O)c1ccc(Cl)cc1
compound 104
CCOC(=O)C1C(=CN(C)C)C(=O)C=CN1S(=O)(=O)c1ccc(Cl)cc1
ethyl 1-(4-chlorophenylsulfonyl)-3-((dimethylamino)methylene)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate

Reactants

CCOC(=O)C1CC(=O)C=CN1S(=O)(=O)c1ccc(Cl)cc1
Compound 103
CCOC(=O)C1CC(=O)C=CN1S(=O)(=O)c1ccc(Cl)cc1
ethyl 1-(4-chlorophenylsulfonyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate
COC(OC)N(C)C
DMF-DMA

Reagents

None

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction mixture was concentrated in vacuo

Procedure

Compound 103 (5.0 g, 15 mmol) was dissolved in DMF-DMA (20 mL) and heated at 100° C. for 30 minutes. The reaction mixture was concentrated in vacuo to yield compound 104 as a yellow oil that was used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732609B2uspto-grants-2010_06