Phthalimide, methylation

As an approach to a better understanding of adhesion mechanisms between polyimide and copper, we have studied the interaction between a set of model molecules for a polyimide and vapor deposited polycrystalline copper. Thin films and adsorbates of benzene, phthalimide, methyl-phthalimide, benzene-phthalimide, and malonamid, which are representative of separate parts of the polyimide repeat unit, were deposited in situ on clean copper and examined by means of X-ray and Ultraviolet photoelectron spectroscopy (XPS and UPS). In contrast to the previously observed bonding to the carbonyl oxygen in polyimide, as Cu is deposited on polyimide, our results show that most of these polyimide model molecules bond to Cu, through electron transfer, with the imide nitrogen atom as the primary reaction site. 

Liaw and coworkers [54] have explored the effect of random versus block copolymerization of hydrophilic and hydrophobic monomers on the polymer and aggregate morphology in solution. ROMP of hydrophobic 5-(octanoate methyl) NBE (NBEMO) and hydrophilic 5-(phthalimide methyl) NBE (NBE-MPI) derivatives was carried out to synthesize amphiphilic copolymers capable of self-assembly (Figure 6.4). The polymer was hydrogenated with... 

Methyl chloride can be converted iato methyl iodide or bromide by refluxing ia acetone solution ia the presence of sodium iodide or bromide. The reactivity of methyl chloride and other aUphatic chlorides ia substitution reactions can often be iacteased by usiag a small amount of sodium or potassium iodide as ia the formation of methyl aryl ethers. Methyl chloride and potassium phthalimide do not readily react to give /V-methy1phtha1imide unless potassium iodide is added. The reaction to form methylceUulose and the Williamson synthesis to give methyl ethers are cataly2ed by small quantities of sodium or potassium iodide. 

Photolysis, apparatus for, 55, 17 Phthalimide, N-amino- [ 1//-Isoindole-1,3-(2//)-dione, 2-amino-, 55, 115 Potassium rew-butoxide [2-Propanol, 2-methyl-, potassium salt], 55,12, 13 Potassium iodide, 55, 71 Potassium permanganate [Permanganic acid, potassium salt], 55,68 Propane, 2,2 dimethyl 1 phenyl, 55, 112 Propane, 2 isocyano-2-methyl-, 55, 96... 

N-Phenyl-phthalimid — in Gegenwart von Acetanhydrid elektrolysiert — liefert unter Ringoffnung 2-(Acetoxy-methyl)-benzanilidl (67% d.Th.) ... 

Method 2. Intimately mix 99 g. of pure phthalic anhydride and 20 g. of urea, and place the mixture in a 1 litre long-necked, round-bottomed flask. Heat the flask in an oil bath at 130-135°. When the contents have melted, effervescence commences and gradually increases in vigour after 10-20 minutes, the mixture suddenly froths up to about three times the original volume (this is accompanied by a rise in temperature to 150-160°) and becomes almost solid. Remove the flame from beneath the bath and allow to cool. Add about 80 ml. of water to disintegrate the solid in the flask, filter at the pump, wash with a little water, and then dry at 100°. The yield of phthalimide, m.p. 233° (. ., it is practically pure) is 86 g. If desired, the phthalimide may be recrystaUised from 1200 ml. of methylated spirit the first crop consists of 34 g. of m.p. 234°, but further quantities may be recovered from the mother liquor. 

The most successful approach to producing an aminomethyl derivative was the Gabriel synthesis. A phthalimide substituent can be introduced by Sn2 displacement of the chloride on 17 with potassium phthalimide under homogeneous conditions in DMF. The reaction is quantitative in all D.F. ranges and the phthalimldo-methyl intermediates, 18, are quite soluble in organic solvents. 

Cyclization occurred at the N-3 atom when 4-(3-bromopropylaruino)-l, 6,7,1 1 b-tctrahydro-2//-pyrimido[6,l -zz -isoquinoline was treated with NaH to give a tetracyclic derivative <2003M1271>. 9,10-Dimethoxy-2-(arylimino)-2,3,6,7-tetrahydro-4//-pyrimido[6,l- ]isoquinolin-4-ones were N-3-alkylated with iV-(ra-bromoalkyl)phthalimides in the presence of K2C03 and a catalytic amount of I2 in boiling 2-butanone in 13-67% yields <2000W020/058308>. Treatment of the 2-[(4-methoxyphenyl)methyl] derivative of 2,3,6,7-tctrahydro-l //,5//-pyrido[3,2,l-/ylqninazolinc-... 

This paper traces in some detail the path which led to the discovery of a new class of herbicides, the 2-(5-oxo-2-imidazolin-2-yl)arylcarboxylates. The journey started when it was found that a phthalimide, a-isopropyl-a-methyl-l,3-dioxo-2-isoindoline-acetamide, had sufficient herbicidal activity to warrant further synthesis effort. This work led to a series of analogs essentially devoid of herbicidal activity yet possessing interesting plant growth regulating effects. Further chemical modifications resulted in the synthesis of two new groups of compounds, imidazoisoindolediones and dihydro-imidazoisoindolediones, and the return of herbicidal activity. The imidazoisoindolediones were in turn transformed into o-(5-oxo-imidazo-lin-2-yl)benzoates, the first members of a very interesting new class of herbicides. 

The fungitoxic N-perhalogenmethylmercapto moiety was introduced for plant protection in 1950 The. two fungicides captan(l) (N-(trichloromethylthio)-tetrahydrophthalimide and folpet(2) (N-(trichlorome-thylthio)phthalimide) contain a perchlorinated methyl-thio group (1 ). About a decade later substitution of fluorine for one of the chlorines in the perchloro-... 

HYDR0XY-3-METHYL-1-PHENYL- (43108-74-3), 65, 5, 12 N-Hydroxymethylphthalimide Phthalimide, N-(hydroxymethyl)- ... 

In the fully and partially unsaturated oxygenated series, the syntheses of 2,5-dimethoxycarbonyl-3,6-diphenyl-l,4-dioxin 231 and 2,6-dimethoxycarbonyl-3,5-diphenyl-l,4-dioxin 232 were recently reported from methyl phenylchloro-pyruvate with potassium phthalimide and sodium imidazolide <2000CHE911>. 

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