Sodium Carbonate → HCID 19350310, compound

HRID 488035Notes

Reaction equation

HRID 488035 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([NH:13][CH2:14][CH:15]=[CH2:16])[CH:11]=[CH2:12].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.C1(C=CC(O)=CC=1)O.CN(C)P(N(C)C)(N(C)C)=O>[CH2:10]([N:13]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:14][CH:15]=[CH2:16])[CH:11]=[CH2:12]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 31279DiallylamineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 19350310HCID 19350310, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 785HydroquinoneCatalystHCID 80021Tetrahexylammonium chlorideCatalystHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 4-fluorobenzaldehyde (16.4 ml, 0.15 mol), diallylamine (20.8 ml, 0.17 mol), sodium carbonate (18.0 g, 0.17 mol), hexamethylphosphoramide (HMPA) (115 ml), hydroquinone (180 mg) and tetrahexyl ammonium chloride (200 mg) was heated under a nitrogen atmosphere for 100 hours. The reaction mixture was cooled and poured into distilled water (1 L). Extraction with toluene (4×300 ml) followed by washing of the combined extracts with distilled water (3×250 ml), drying over anhydrous magnesium sulfate, filtration and concentration in vacuo yielded 32 g as a viscous yellow oil. Fractional distillation at 0.8 mm Hg gave 15 g (50%) of 4-(N,N'-diallylamino)benzaldehyde as a pale yellow oil.

Workup

  1. temperaturewas heated under a nitrogen atmosphere for 100 hours
  2. temperatureThe reaction mixture was cooled
  3. additionpoured
  4. distillationinto distilled water (1 L)
  5. extractionExtraction with toluene (4×300 ml)
  6. washby washing of the combined extracts with distilled water (3×250 ml)
  7. dry with materialdrying over anhydrous magnesium sulfate, filtration and concentration in vacuo
  8. customyielded 32 g as a viscous yellow oil
  9. distillationFractional distillation at 0.8 mm Hg

Sources & evidence

ORD record
ord-9904b943804f4e63805bc1c14ffe5b8b
Source dataset
uspto-grants-1994_03
Patent number
US05298588

Reaction notes

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