N-Phenyl-p-phenylenediamine → N,N'-Diphenyl-P-Phenylenediamine

HRID 2266983Notes

Reaction equation

HRID 2266983 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([NH:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC([O-])(C)C.[Na+]>O1CCOCC1>[C:2]1([NH:21][C:18]2[CH:17]=[CH:16][C:15]([NH:14][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:20][CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 7964ChlorobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 6319N,N'-Diphenyl-P-PhenylenediamineYield 99.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Following general procedure F, a mixture of chlorobenzene (102 μL, 1.0 mmol), N1-phenylbenzene-1,4-diamine (221 mg, 1.2 mmol), NaOt-Bu (192 mg, 2.0 mmol), 10 (8 mg, 1 mol %), 1 (5 mg, 1 mol %), and dioxane (1 mL) was heated to 80° C. for 2 h. The crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 0-50% EtOAc/Hexane) to provide the title compound as a off-white solid (260 mg, 99%), mp 152-154° C. 1H NMR (300 MHz, CDCl3) δ: 7.27 (t, J=7.5 Hz, 4H), 7.08 (s, 4H), 7.00 (d, J=8.0 Hz, 4H), 6.90 (t, J=7.5 Hz, 2H), 5.59 (s, 2H) ppm. 13C NMR (75 MHz, CDCl3) δ: 144.7, 137.4, 129.6, 121.2, 120.2, 116.5 ppm. IR (neat, cm−1): 3389, 1601, 1512, 1496, 1382, 1313, 1271, 820, 742, 695. Anal. Calcd. for C18H16N2: C, 83.04; H, 6.19. Found: C, 82.81; H, 6.22.

Workup

  1. customThe crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 0-50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-f4e76a69edf74fdd886674ad568b0b80
Source dataset
uspto-grants-2010_12
Patent number
US07858784B2

Reaction notes

Loading…