Isoindoline derivative
A technology of isoindoline and derivatives, applied in the field of isoindoline derivatives, can solve problems such as unsatisfactory
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Embodiment 1
[0301] a) At room temperature, 33.8 g (0.19 mol) of p-aminobenzenesulfonic acid was added to 66 g (0.19 mol) of the solution prepared in Synthesis Example 1 and 50 ml of methanol was added. The yellow suspension was stirred overnight at room temperature and then at 50°C for 1 hour. The suspension was cooled to room temperature and filtered. The solid is washed with deionized water and dried at 60° C. / 100 mbar to give 48.4 g of product of formula (XVIa), which may be partly present as the corresponding ammonium salt. The molecular weight of the product was confirmed by MALDI-TOF-MS (M - 300e / z, M + 302e / z).
[0302]
[0303] b) 40.0 g (0.13 mol) of the product of example 1 a) and 16.9 g (0.13 mol) of barbituric acid were suspended in 1 L of glacial acetic acid. The yellow suspension was stirred overnight at 110°C, cooled to 40°C and filtered. The solid was washed with methanol and dried at 70[deg.] C. / 100 mbar to give 48.4 g of a yellow product of formula (XVIb), which ...
Embodiment 2
[0306] a) At room temperature, 34.3 g (0.19 mol) of 3-aminobenzenesulfonic acid (0.19 mol) was added to 66 g (0.19 mol) of the solution prepared in Synthesis Example 1 and 50 ml of methanol was added. The yellow suspension was stirred overnight at room temperature, then 100 ml of methanol were added and stirred at 50° C. for 1 hour. The suspension was cooled to room temperature and filtered. The solid is washed with deionized water and dried at 60° C. / 100 mbar to give 36.3 g of product of formula (XVIIa), which may be partly present as the corresponding ammonium salt. The molecular weight of the product was confirmed by MALDI-TOF-MS (M - 300e / z, M + 302e / z).
[0307]
[0308] b) 30.0 g (0.10 mol) of the product of example 2a) and 16.9 g (0.10 mol) of barbituric acid were suspended in 500 ml of glacial acetic acid. The yellow suspension was stirred overnight at 110°C, cooled to 40°C and filtered. The solid was washed with methanol and dried at 70[deg.] C. / 100 mbar to gi...
Embodiment 3-1
[0311] a) A mixture of 65 g (0.45 mol) of diiminoisoindoline and 100 g (0.45 mol) of 5-aminonaphthalenesulfonic acid (>90%) was suspended in 350 ml of methanol. The mixture was heated to reflux with stirring. After 5 hours the mixture is cooled to room temperature, the solid is filtered, washed with 1000 ml of water and dried at 60° C. / 100 mbar, yielding 87 g of a brown-yellow product of the formula (XVIIIa), which may be partly present as the corresponding ammonium salt. Yield 145 g (84%). The molecular weight of the product was confirmed by MALDI-TOF-MS (M - 351e / z, M + 352e / z).
[0312]
[0313] b) 100.0 g (0.29 mol) of the product of example 3a) and 36.5 g (0.29 mol) of barbituric acid were suspended in 350 ml of glacial acetic acid. The suspension was stirred at reflux for 5 hours, then cooled to room temperature and filtered. The brownish-yellow solid is washed with 200 ml of water and dried at 80° C. / 125 mbar, yielding 99 g of a yellowish product of the formula ...
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