3,3′-[Sulfonylbis(4,1-phenyleneoxy)]bis[benzenamine]

beige to brown powder

In the next step, a 300 ml glass reaction vessel was charged with 25 grams (0.055 mol) of crude 4, 4'-bis(3-nitrophenoxy)diphenylsulfone, 2.5 grams of active carbon, 0.25 gram of ferric chloride hexahydrate and 130 ml of ethyleneglycol monomethylether, and refluxed for 30 minutes with stirring. Specific examples of amine curing agents useful in this invention are given below:...1, 3-bis(3-aminophenoxy)benzene1, 3-bis(4-aminophenoxy)benzene1, 4-bis(3-aminophenoxy)benzene1, 4-bis(4-aminophenoxy)benzenebis[4-(3-aminophenoxy)phenyl]sulfonebis[4-(4-aminophenoxy)phenyl]sulfone4, 4'-bis(3-aminophenoxy)biphenyl4, 4'-bis(4-aminophenoxy)biphenyl...180 g of the primary diamine compound 'Compound 1A' and 900 g of ethyl acetate were placed in a 2 liter four-necked flask, and 112 g of salicylaldehyde was added dropwise at room temperature. After the dropwise addition, the mixture was stirred under refluxing ethyl acetate for 21 hours. As a result, crystals precipitated during stirring. After completion of the reaction, the reaction solution was cooled to 4 ° C., filtered, and the separated crystals were dried to obtain 234 g of diimine compound 'Compound 1B' having a purity of 99.7percent (gel permeation chromatography analysis method). Yield 87.0percent (Yield relative to 'Compound 1A)36.2 g of bis {4- (3-aminophenyloxy) phenyl} sulfone, 204.4 g of ethyl acetate and 25.1 g of 5-methyl salicylaldehyde were placed in a 500 milliliter four-necked flask. And the mixture was stirred under refluxing ethyl acetate for 33.5 hours. On the way, distillation was carried out at 80 ° C. under atmospheric pressure, and 78.4 g of ethyl acetate was distilled off. Crystals precipitated during the reaction. After completion of the reaction, the reaction solution was cooled to 4 ° C., filtered, and the separated crystals were dried to give 99.7percent purity (gel permeation chromatography analysis)Of 54.0 g of bis {4- {3- [2- (2-hydroxy-5-methylphenyl) -1-azavinyl] phenoxy} phenyl} sulfone. Yield 96.4percent (yield based on bis {4- (3-aminophenyloxy) phenyl} sulfone)Example 5Preparation of 4, 4'-bis[3-(N-dimethylvinylsilyl)aminophenoxy]diphenyl sulfoneUnder nitrogen atmosphere, to two-necked flask successively added In the next step, a 300 ml glass reaction vessel was charged with 25 grams (0.055 mol) of crude 4, 4'-bis(3-nitrophenoxy)diphenylsulfone, 2.5 grams of active carbon, 0.25 gram of ferric chloride hexahydrate and 130 ml of ethyleneglycol monomethylether, and refluxed for 30 minutes with stirring. After dropping 11 grams (0.22 mol) of hydrazine hydrate at 70-80° C. during 2 hours, the mixture was stirred for further 6 hours at 70-80° C., followed by cooling and filtering to remove the catalyst. The solvent was distilled off in a vacuum and then 12 grams of 35percent hydrochloric acid and 73 ml of water were added to the residue which was dissolved by warming. Hydrochloride was separated by cooling after addition of 7 grams of sodium chloride. The hydrochloride was filtered and recrystallized again from 10percent aqueous sodium chloride solution and then dissolved into 100 ml of 50percent aqueous IPA solution and filtered after adding 1 gram of active carbon. The filtrate was neutralized with aqueous ammonia to separate crystals which were filtered, washed with water and dried. By recrystallizing from ethanol, 18.8 grams (79percent yield) of

Molecular Weight:432.5
XLogP3:4.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:432.11437830
Monoisotopic Mass:432.11437830
Topological Polar Surface Area:113
Heavy Atom Count:31
Complexity:601
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes