1,4-Dioxane → HCID 67050638, compound

HRID 1629121Notes

Reaction equation

HRID 1629121 reaction equation
Cl[C:2](=[N:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][C:18]#[N:19])[C:3]([O:5][CH3:6])=[O:4].O1CCOCC1>[Sn].C(=O)([O-])[O-].[Ag+2]>[N:7]1[N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH2:16][CH2:17][C:18]2=[N:19][C:2]=1[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 86711716Methyl 2-chloro-2-(2-(2-(2-cyanoethoxy)phenyl)hydrazono)acetate

Product 1

HCID 67050638HCID 67050638, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 5352426Tin atomSolvent

Procedure

To chlorohydrazone 85 (2.87 g, 10.2 mmol) in a 200 mL flask was added 1,4-dioxane (100 mL) and silver carbonate (4.22 g, 15.3 mmol) under nitrogen (FIG. 18). The flask was fitted with a reflux condenser, and wrapped in tin foil (to keep in the dark). Next, the reaction was refluxed while stirring for 4 hours. Then, the reaction was filtered, concentrated, and purified by silica gel chromatography to provide ester 86 in 7% yield over two steps. 1H NMR (500 MHz, CDCl3) δ 8.19 (dd, J=8.2, 1.4 Hz, 1H), 7.31 (td, J=8.0, 1.6 Hz, 1H), 7.25-7.20 (m, 1H), 7.18 (dd, J=8.1, 1.3 Hz, 1H), 4.50 (t, J=5.7 Hz, 2H), 4.03 (s, 3H), 3.50 (t, J=5.7 Hz, 2H). LRMS m/z Calcd. for C12H11N3O3: 245.08004, found: 246.1 [M+1].

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperatureNext, the reaction was refluxed
  3. filtrationThen, the reaction was filtered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9bf65b915a2c4a57990b48884f3dd9ca
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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