Formaldehyde → HCID 20446127, compound

HRID 2418298Notes

Reaction equation

HRID 2418298 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]([C:11]1[C:15]([CH3:16])=[CH:14][S:13][C:12]=1[CH3:17])[CH:7]([CH3:10])[C:8]#[CH:9])=[O:5].C=O.[CH:20](NC(C)C)(C)C>O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]([N:6]([C:11]1[C:15]([CH3:16])=[CH:14][S:13][C:12]=1[CH3:17])[CH:7]([CH3:10])[CH:8]=[C:9]=[CH2:20])=[O:5]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7912DiisopropylamineHCID 13341209HCID 13341209, compound

Product 1

HCID 20446127HCID 20446127, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 10.0 g (0.04 mol) 2-methoxy-N-(2,4-dimethylthien-3-yl)-N-(1-butin-3-yl)acetamide in 80 ml dioxan are added 1.92 g (0.064 mol) paraformaldehyde, 4.85 g (0.048 mol) diisopropylamine and 1.89 g cuprous bromide and the mixture heated to reflux for 6 hours. The mixture is cooled to room temperature, filtered, evaporated in vacuo, the residue partitioned between ethylacetate and 1 M aqueous citric acid solution, the organic phase separated, washed subsequently with a saturated aqueous NaHCO3 -solution, water, is dried over MgSO4 and the solvent evaporated in vacuo.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 6 hours
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customthe residue partitioned between ethylacetate and 1 M aqueous citric acid solution
  6. customthe organic phase separated
  7. washwashed subsequently with a saturated aqueous NaHCO3 -solution, water
  8. dry with materialis dried over MgSO4
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-80be87e8956446fd9261ef80bdcb1621
Source dataset
uspto-grants-1984_09
Patent number
US04472425

Reaction notes

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