General Papers ARKIVOC 2006 (xiii) 8-15
purchased from the Fluka (montmorillonite KSF and montmorillonite K-10 clays) and Aldrich (anhydrides, diamines and solvents) chemical companies. The relevant products were characterized by the comparison of their spectra (IR, 1H NMR and 13C NMR), elemental analysis
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and physical data with the authentic samples. H NMR and C NMR spectra were recorded on a FT-NMR JEOL FX 90Q spectrometer. Chemical shifts were measured in ppm from TMS. DMSO-d6 was used as a solvent as well as the internal standard. The IR spectra were obtained on a Perkin Elmer FT IR GX instrument in KBr discs. N- Phthalimidophthalimide (2a). In a typical experiment, phthalic anhydride (2.2 mmole, 0.33 g) and montmorillonite KSF clay (1g) mixed, grinded properly, placed in a clean and dry beaker and hydrazine hydrate (1 mmole, 0.05 g) was then added. The reaction mixture preheated in a microwave oven for 1 min (power 600 W) and the heating continued for 4 min (power 780 W) to complete the reaction which was monitored by TLC using n-hexane/acetone as an eluent (3:7). The reaction mixture were allowed to cool to the room temperature and the resulting product extracted into CH2Cl2 (2×20 mL). The montmorillonite KSF clay was filtered off and the solvent removed by rotary. Solid clay portion was washed with methanol and dried at 120oC under the reduced pressure for 5h to be reused in the subsequent reactions. The obtained product was washed with distilled and warm water, dried in the oven (50oC, 4h) and recrystallized from acetic acid to collect N-phthalimidophthalimide (2a) as colorless prisms (9.66 g , 82%), mp >300oC (lit.22e 44.5%, mp 311-313oC, reaction time 1h in refluxing with acetic acid). .R (KBr) cm-1:
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3028, 1783, 1745, 1657, 1601, 1493, 1377, 683. H NMR (DMSO-d6): d7.71 (4H, dd, Ar), 8.15 (4H, d, Ar), 13C NMR (DMSO-d6): d 127.4, 132.0, 132.3, 165.5. Anal. Calcd. for C16H8N2O4: C, 65.75; H, 2.80; N, 9.60. Found: C, 65.14; H, 2.23; N, 9.31%. Bismaleimide (1a). Yield 86%, mp 256-258oC (lit.22a 259-260oC). .R (KBr) cm-1: 3026, 2938,
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2918, 1780, 1714, 1612, 1385, 709. H NMR (DMSO-d6): d 6.95 (4H, s, Vinilic), 13C NMR (DMSO-d6): d 136.4, 162.9. Anal. Calcd. for C8H4N2O4: C, 50.0; H, 2.08; N, 14.58. Found: C, 49.37; H, 2.43; N, 14.06%. 1,1'-Ethylenebismaleimide (1b). Yield 74%, mp 187-190oC (lit.22b 190-192oC). .R (KBr) cm-1:
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2926, 1774, 1709, 1619, 1432, 719. H NMR (DMSO-d6): d 3.74 (4H, t, 2CH2), 6.92 (4H, s, Vinilic), 13C NMR (DMSO-d6): d 39.4, 136.6, 164.5. Anal. Calcd. for C10H8N2O4: C, 54.55; H, 3.66; N, 12.72. Found: C, 54.81; H, 3.97; N, 12.47%. 1,1'-Hexamethylenebismaleimide (1c). Yield 68%, mp 136-138oC (lit.22b 139-140oC). .R (KBr)
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cm-1: 2914, 1768, 1712, 1623, 1468, 1378, 695. H NMR (DMSO-d6): d 1.39 (2H, t, 3-CH2), 1.55 (2H, m, 2-CH2), 3.48 (2H, m, 1-CH2), 13C NMR (DMSO-d6): d 24.5, 28.7, 40.8, 136.5, 164.6. Anal. Calcd. for C14H16N2O4: C, 60.86; H, 5.84; N, 10.14. Found: C, 60.07; H, 5.36; N, 9.55%. 1,1'-(1,4-Phenylene)bismaleimide (1d). Yield 89%, mp >300oC (lit.22b 346-350oC). .R (KBr)
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cm-1: 3461, 3435, 3169, 3107, 1778, 1717, 1612, 1602, 1457, 1398, 699. H NMR (DMSO-d6): d
7.2 (4H, s, Vinilic), 7.62-7.40 (4H, d, C6H4), 13C NMR (DMSO-d6): d 119.8, 132.5, 136.0, 163.3. Anal. Calcd. for C14H8N2O4: C, 62.69; H, 3.01; N, 10.45. Found: C, 63.18; H, 3.49; N, 10.12%. ISSN 1424-6376 Page 12 ©ARKAT
