Aniline → N-(5-Chloro-2-hydroxy4-nitrophenyl)-N'-(4-(4-pyridinylmethyl)phenyl)urea

HRID 2110086

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.NC1C=CC=CC=1.[NH2:22][C:23]1[CH:28]=[C:27]([Cl:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][C:24]=1[OH:33].C[CH2:35][O:36]C(C)=O>C(Cl)Cl>[Cl:29][C:27]1[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][C:24]([OH:33])=[C:23]([NH:22][C:35]([NH:12][C:11]2[CH:10]=[CH:9][C:8]([CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:14][CH:13]=2)=[O:36])[CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 42.5 °C

Versuchsvorschrift

A solution of 4-(4-pyridinylmethyl)aniline (0.300 g, 1.63 mmol) and N,N′-carbonyldiimidazole (0.268 g, 1.65 mmol) in CH2Cl2 (10 mL) was stirred at room temp. for 1 h at which time TLC analysis indicated no starting aniline. The reaction mixture was then treated with 2-amino-4-chloro-5-nitrophenol (0.318 g, 1.65 mmol) and stirred a 40-45° C. for 48 h. The resulting mixture was cooled to room temp. and diluted with EtOAc (25 mL). The resulting precipitate was separated to give the desired product (0.416 g, 64%): TLC (50% acetone/50% CH2Cl2) Rf 0.40; 1H-NMR (DMSO-d6) δ 3.90 (s, 2H), 7.18 (d, J=8.4 Hz, 2H), 7.21 (d, J=6 Hz, 2H), 7.38 (d, J=8.4 Hz, 2H), 7.54 (s, 1H), 8.43-8.45 (m, 3H), 8.78 (s, 1H), 9.56 (s, 1H), 11.8 (br s, 1H); FAB-MS m/z (rel abundance) 399 ((M+H)+, 10%). B6. General Method for the Synthesis of Symmetrical Diphenyl Ureas as Side-Products of Urea Forming Reactions

Aufarbeitung

temperatureThe resulting mixture was cooled to room temp.
customThe resulting precipitate was separated

Quellen und Nachweise

ORD-Eintrag: ord-0d3075ef925747b0b9385f5d898d3f2c
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07517880B2

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