An efficient and convenient protocol for the synthesis of diaminotriarylmethanes
499
4-[Bis[4-(diethylamino)phenyl]methyl]-2-methoxyphenol
(3ac, C28H36N2O2)
References
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IR (KBr): v = 3,392, 2,970, 2,932, 2,870, 1,612, 1,558,
1,514, 1,464, 1,448, 1,396, 1,375, 1,356, 1,265, 1,198,
1,151, 1,124, 1,094, 1,078, 1,034, 1,013, 881, 808 cm-1
;
1H NMR (500 MHz, CDCl3): d = 1.11 (t, J = 7.5 Hz,
12H), 3.28 (q, J = 7.5 Hz, 8H), 3.73 (s, 3H), 5.25 (s, 1H),
5.56 (br s, 1H), 6.58 (d, J = 8.5 Hz, 4H), 6.58 (d,
J = 8.5 Hz, 4H), 6.61 (dd, J = 8.5, 1.5 Hz, 1H), 6.69 (d,
J = 1.5 Hz, 1H), 6.79 (d, J = 8.5 Hz, 1H), 6.94 (d,
J = 8.5 Hz, 4H) ppm; 13C NMR (125 MHz, CDCl3):
d = 12.5, 44.2, 54.5, 55.6, 111.7, 112.0, 113.7, 121.9,
129.8, 131.9, 137.5, 143.5, 145.9, 146.1 ppm.
4,40-[(2,4-Dichlorophenyl)methylene]bis-
(N,N-diethylaniline) (3ad, C27H32Cl2N2)
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IR (KBr): v = 3,419, 3,092, 2,968, 2,870, 1,611, 1,585,
1,560, 1,518, 1,466, 1,396, 1,354, 1,267, 1,199, 1,126,
1
1,078, 1,028, 1,013, 953, 862, 843, 814, 800 cm-1; H
NMR (500 MHz, CDCl3): d = 1.12 (t, J = 7.0 Hz, 12H),
3.32 (q, J = 7.0 Hz, 8H), 5.66 (s, 1H), 6.58 (d, J = 8.5 Hz,
4H), 6.88 (d, J = 8.5 Hz, 4H), 6.97 (d, J = 8.0 Hz, 1H),
7.10 (dd, J = 8.0, 2.0 Hz, 1H), 7.34 (d, J = 2.0 Hz, 1H)
ppm; 13C NMR (125 MHz, CDCl3): d = 12.8, 44.4, 51.2,
111.8, 126.7, 129.2, 129.7, 129.8, 130.3, 132.1, 135.1,
142.3, 146.5 ppm.
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4,40-[(3,4-Dichlorophenyl)methylene]bis-
(N,N-diethylaniline) (3ae, C27H32Cl2N2)
IR (KBr): v = 3,420, 2,966, 2,928, 2,868, 1,611, 1,564,
1,518, 1,466, 1,396, 1,375, 1,267, 1,199, 1,154, 1,126,
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1,028, 1,013, 953, 908, 862, 843, 814 cm-1 1H NMR
;
(500 MHz, CDCl3): d = 1.13 (t, J = 7.0 Hz, 12H), 3.31 (q,
J = 7.0 Hz, 8H), 5.25 (s, 1H), 6.59 (d, J = 8.5 Hz, 4H),
6.90 (d, J = 8.5 Hz, 4H), 6.98 (dd, J = 8.5, 2.0 Hz, 1H),
7.24 (d, J = 2.0 Hz, 1H), 7.29 (d, J = 8.5 Hz, 1H) ppm;
13C NMR (125 MHz, CDCl3): d = 12.7, 44.4, 54.3, 111.8,
128.9, 129.6, 129.9, 130.1, 130.3, 131.3, 132.1, 146.4 ppm.
4-[Bis[4-(diethylamino)phenyl]methyl]benzaldehyde
(3ai, C28H34N2O)
IR (KBr): v = 3,412, 2,970, 2,929, 1,701, 1,605, 1,589,
1,543, 1,518, 1,464, 1,447, 1,373, 1,356, 1,198, 1,142,
;
1,067, 1,015, 951, 929, 907, 863, 808 cm-1 1H NMR
(500 MHz, CDCl3): d = 1.13 (t, J = 7.0 Hz, 12H), 3.31
(q, J = 7.0 Hz, 8H), 5.38 (s, 1H), 6.59 (d, J = 9.0 Hz,
4H), 6.92 (d, J = 9.0 Hz, 4H), 7.33 (d, J = 8.0 Hz, 2H),
7.76 (d, J = 8.5 Hz, 2H), 9.96 (s, 1H) ppm; 13C NMR
(125 MHz, CDCl3): d = 12.7, 44.3, 55.3, 111.7, 129.7,
130.1, 130.2, 130.4, 134.4, 146.4, 153.4, 192.1 ppm.
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Acknowledgments We are thankful to the National Natural Science
Foundation of China (20872025 and 21072042) and the Nature Sci-
ence Foundation of Hebei Province (B2008000149) for financial
support of this work.
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