Sodium hydride → HCID 178498783, compound

HRID 59954Notes

Reaction equation

HRID 59954 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[C:12]([O:14]C)=O.C(O)(=O)C.[CH:20](=[NH:22])[NH2:21].[H-].[Na+]>O1CCOCC1>[OH:14][C:12]1[C:3]2[CH:4]=[N:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]=2[N:21]=[CH:20][N:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 160693Formamidine acetateHCID 22019198Dimethyl 4-chloropyridine-3,5-dicarboxylate

Product 1

HCID 178498783HCID 178498783, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of dimethyl 4-chloropyridine-3,5-dicarboxylate (0.6 g, 2.6 mmol) and formimidamide acetate (0.82 g, 7.8 mmol) in dioxane (20 mL) was added NaH (0.31 g, 7.8 mmol). The resulting mixture was refluxed for 48 hours, cooled to RT. The precipitate was filtered, and washed with EA to afford the title compound as grey solid (yield 56.1%).

Workup

  1. temperatureThe resulting mixture was refluxed for 48 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with EA

Sources & evidence

ORD record
ord-d8e04bf101054bd485f02b6b7bb4af81
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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