2,5-Dimethoxytetrahydrofuran → HCID 2807914, compound

HRID 1779480Notes

Reaction equation

HRID 1779480 reaction equation
Cl.Cl[C:3]1[CH:8]=CN=[CH:5][CH:4]=1.COC1CCC(OC)O1.[CH3:18][C:19]1[C:20]([NH2:28])=[C:21]([C:24]([O:26][CH3:27])=[O:25])[S:22][CH:23]=1>O1CCOCC1>[CH3:18][C:19]1[C:20]([N:28]2[CH:5]=[CH:4][CH:3]=[CH:8]2)=[C:21]([C:24]([O:26][CH3:27])=[O:25])[S:22][CH:23]=1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 818524-Chloropyridine hydrochlorideHCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylate

Product 1

HCID 2807914HCID 2807914, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

43.8 g (0.292 mol) of 4-chloropyridine hydrochloride and 38.59 g (0.292 mol) of 2,5-dimethoxytetrahydrofuran are stirred for 10 minutes at room temperature in 600 ml of dioxane. 50 g (0.292 mol) of methyl 4-methyl-3-aminothiophene-2-carboxylate are added and the suspension is heated at reflux for 3 hours. The dioxane is removed under reduced pressure, and the residue is taken up in 1 liter of water and then extracted with 1 liter of diethyl ether. The ethereal phase is washed with water, decanted off, dried over magnesium sulfate, rendered colourless with animal charcoal and concentrated under reduced pressure to yield the title compound.

Workup

  1. temperaturethe suspension is heated
  2. temperatureat reflux for 3 hours
  3. customThe dioxane is removed under reduced pressure
  4. extractionextracted with 1 liter of diethyl ether
  5. washThe ethereal phase is washed with water
  6. customdecanted off
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-135754a7467042428d2c4ac7ac980c11
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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