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

HRID 259213

反応式

HRID 259213 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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 Dry Ice-cooled condenser) for 1.25 hr, giving a dark brown solution having a small 31P nmr peak at -126.2 ppm for unreacted phosphite and a large product peak at -18.4 ppm (~1:5 areas). The reaction mixture is stripped to 130°/3mm. The residue is diluted with 200 ml of acetonitrile and 10 g of H2O, and this solution is warmed at reflux for 3 hr. Solid that separates during warming is recrystallized from acetic acid-water to give a white solid; mp 186°-187° dec; P31 nmr -21.6 ppm; 1H nmr δ10.0 (s, 2, OH), 7.3 (m, 10, C 6 H5), 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.

後処理

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

出典と根拠

ORDレコード
ord-b771fd40c53d4ad99a4beb553179bb79
出典データセット
uspto-grants-1977_07
特許番号
US04036913

関連ノート

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