N,N0-(1,2-Phenylene)bis(2-chloroacetamide) 47d. To a stirred
solution of o-phenylenediamine (1 g, 5.62 mmol) in dry
CH2Cl2 (30 mL) chloroacetyl chloride (1.07 mL, 13.48 mmol)
was added followed by addition of Et3N (1.87 mL, 13.48 mmol).
After stirring the reaction mixture for 1 h at room temperature,
solvent was evaporated under reduced pressure. The reaction
mixture was neutralized with NaHCO3 solution and extracted
with CHCl3 (3 ꢁ 30 mL). The combined organic layer was
dried over anhydrous Na2SO4 and concentrated on rotary
evaporator. Purification of the mixture by silica gel column
chromatography using 3% methanol in chloroform yielded
compound 4 in 91% yield (2.2 g): mp 191 1C; 1H NMR
(400 MHz, CDCl3 containing one drop of DMSO-d6) d 9.40
(s, 2H, amide NH), 7.53–7.50 (m, 2H), 7.28–7.24 (m, 2H), 4.20
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(s, 4H); FTIR (KBr) 3253, 3195, 1674, 1655 cmꢀ1
.
Receptor 1. To a stirred solution of 4 (0.100 g, 0.382 mmol)
in DMF (2 mL), compound 3 (0.241 g, 0.919 mmol) in dry
CH3CN (10 mL) was added. The reaction mixture was
refluxed with stirring for 5 days under nitrogen atmosphere.
After completion, the reaction mixture was cooled to room
temperature and filtered. The precipitate was washed with
CH3CN for several times to give pure dichloride salt 5
(0.230 g, yield 76%). The dichloride salt 5 (0.100 g, 0.127 mmol)
was dissolved in 2 mL hot CH3OH and NH4PF6 (0.056 g,
0.34 mmol) was added to it in one portion. After stirring the
reaction mixture for 20 min water was added. The precipitate
was filtered and washed with water to give 1 (0.115, yield
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1
90%); mp 200 1C; H NMR (400 MHz, DMSO-d6) d 11.42
(s, 2H), 10.06 (s, 2H), 9.40 (s, 2H), 8.56 (d, 2H, J = 8 Hz), 8.35
(d, 2H, J = 8 Hz), 8.05–8.00 (m, 4H), 7.89 (d, 2H, J = 8 Hz),
7.81 (d, 2H, J = 8 Hz), 7.53–7.43 (m, 10H), 7.20 (br s, 2H),
5.52 (s, 4H), 4.26 (s, 4H); 13C NMR (100 MHz, DMSO-d6)
d 170.5, 163.4, 140.7, 138.5, 136.0, 134.5, 133.2, 131.7, 131.1,
130.0, 128.4, 128.0, 127.5, 126.1, 125.9, 125.7, 125.4, 125.2,
124.0, 62.4 (one carbon in aromatic region is unresolved and
one carbon is overlapped with carbons of solvent d6-DMSO);
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10.1039/C0CS00169D.
FTIR (KBr) 3384, 3099, 1697, 1595, 1551, 1508, 1457 cmꢀ1
;
Mass
(EI):
859.7
(M–PF6ꢀꢀ1)+,
713.2,
437.2;
C44H38N6O4.2PF6 calcd. C 52.60, H 3.81, N 8.36; found C
52.49, H 3.78, N 8.26.
Acknowledgements
We thank CSIR, New Delhi, India for financial support.
I. S. also thanks CSIR for providing a research fellowship.
Notes and references
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Rev., 2003, 103, 4419; (e) A. P. de Silva, H. Q. N. Gunaratne,
c
1402 New J. Chem., 2011, 35, 1397–1402
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011