Reaktion #1663471

Reaktionsgleichung

1,3-dimethylurea

triphenyl phosphite

3-methylthiopropionaldehyde

toluene

→

1-(1,3-Dimethylureido)-3-(methylthio)propylphosphonic acid

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis warmed to 75°
2. 2
   Temperaturthe temperature increases rapidly to 120°
3. 3
   TemperaturAfter further warming at 105° for 1 hr
4. 4
   SonstigeAfter the solvent and most of the byproduct phenol are removed
5. 5
   Sonstigeby stripping to 110°
6. 6
   workup.DISSOLUTIONis dissolved in 75ml of acetonitrile
7. 7
   Temperatur10g of water, and this solution is refluxed for 3 hr
8. 8
   Sonstigeto evaporate to dryness
9. 9
   Extraktionthe residue is extracted with ether
10. 10
    Sonstigewith hot acetonitrile and recrystallized twice from acetic acid
11. 11
    Sonstigeto give a white solid

Vorschrift

When a mixture of 0.5 mole each of 1,3-dimethylurea, triphenyl phosphite, and 3-methylthiopropionaldehyde in 100g of toluene is warmed to 75°, a reaction is initiated and the temperature increases rapidly to 120°. After further warming at 105° for 1 hr, the resulting yellow solution has a 31P nmr signal only at -28.2 ppm. After the solvent and most of the byproduct phenol are removed by stripping to 110°/1mm, one-third of the residue is dissolved in 75ml of acetonitrile and 10g of water, and this solution is refluxed for 3 hr. The reaction mixture is allowed to evaporate to dryness, and the residue is extracted with ether and then with hot acetonitrile and recrystallized twice from acetic acid to give a white solid: mp 164.5°-167°; 31P nmr (DMSO-d6) -21.4 ppm; 1H nmr δ9.6 (broad, 2, OH), 4.5 (m, 1, PCH), 2.8 (s, NCH3), 2.6 (s, NCH3), 2.0 (s, SCH3), 1.9-2.6 (m, CH2CH2S).

Quelle