Acetaldehyde → 1-(3,3-Diphenylureido)ethylphosphonic acid

HRID 1415282

Reaktionsgleichung

Reaktionsgleichung von HRID 1415282
[CH:1](=O)[CH3:2].[C:4]1([N:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([NH2:13])=[O:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[P:20]([O:35]C1C=CC=CC=1)([O:28]C1C=CC=CC=1)[O:21]C1C=CC=CC=1.C(=O)=O.P([O-])([O-])[O-]>C(#N)C.O.C1C=CC=CC=1>[C:4]1([N:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:12])[NH:13][CH:1]([P:20](=[O:21])([OH:35])[OH:28])[CH3:2])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

9

Edukt 5

HCID 177AcetaldehydeHCID 280Carbon DioxideHCID 7540Triphenyl phosphiteHCID 336031,1-DiphenylureaHCID 107908Phosphite

Produkt 1

HCID 214235511-(3,3-Diphenylureido)ethylphosphonic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Freshly distilled acetaldehyde (0.22 mole) is added during 0.5 hr to a stirred solution of 0.1 mole each of 1,1-diphenylurea and triphenyl phosphite in 130g of benzene at 60° C. The solution is warmed at reflux (65°-70° with a Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unrected phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm and the residue diluted with 200 ml of acetonitrile and 10g of H2O, and this solution warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give the product as a white solid: mp 186°-187° C dec; P31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C6H5), 5.4 (d of d, 1, J = 9 and 5Hz, NH), 4.1 (m, 1, CH), 1.3 (d, of d, 3, J = 16 and 7 Hz, CH3); acidity 2.00 equiv/mole, pK1 = 2.20, pK2 = 8.62.

Aufarbeitung

  1. temperatureThe solution is warmed
  2. temperaturecooled condenser) for 1.25 hr
  3. customgiving a dark brown solution
  4. customis stripped to 130°
  5. temperaturethis solution warmed
  6. temperatureat reflux for 3 hr
  7. temperatureSolid that separates during warming
  8. customis recrystallized from acetic acid-water

Quellen und Nachweise

ORD-Eintrag
ord-89a33b6793d546c3b360885512ce11d6
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04003965

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