Benzene → Diphenyl alpha-(3,3-diphenylureido)-4-nitrobenzylphosphonate

HRID 259212

Reaktionsgleichung

[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)([O-:19])=[O:18].[P:28]([O:43]C1C=CC=CC=1)([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]1([N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:9])[NH:10][CH:24]([P:28](=[O:43])([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:23]2[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 87 °C

Versuchsvorschrift

A mixture of 21.2g (0.1 mole) of 1,1-diphenylurea, 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87° C.) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), -127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579).

Aufarbeitung

temperaturewarmed
customto give a light yellow solution
customMost of the benzene is removed at reduced pressure, and ether
stirringis stirred into the yellow oil
customto separate after a few minutes
customA portion is recrystallized from acetonitrile
customto give a white solid

Quellen und Nachweise

ORD-Eintrag: ord-9e76a56994ea4e6c8c3c87f8f119245c
Quelldatensatz: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04036913

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