1.5- Dimethyl-2-pyrrolidinone

For the preparation of the triazine membranes, the entire solid support (cellulose or polypropylene membrane) was treated with a 5 m solution of the corresponding amine in l-methyl-2-pyrrolidinone (NMP) and a 1 m solution of cesium phenolate in dimethyl sulfoxide (2 p L of each at one spot) and subsequently heated in a domestic microwave oven for 3 min. After washing the support successively with... 

It is evident that some leeway is available in the substituents tolerable in the m-position. The bronchodilator sulfonterol (28) is descended from this observation. Chloromethylanisole (29) is reacted with methylmereaptan to give 30, and the newly introduced group is oxidized to the methyl-sulfonyl moiety of 31 with hydrogen peroxide. Ether cleavage, acetylation and Fries rearrangement of the phenolic acetate produces 32, which is next brominated with pyrrolidinone hydrobromide tribromide and then oxidized to the glyoxal (33) with dimethyl sulfoxide. 

Generally speaking, if achiral dopant acid is a strong acid, that is, pKa < 3, and soluble in water, ZV-mcthyl-2-pyrrolidinone, dimethyl sulfoxide, or N,N -dimethylformamide can be used to generate helical polyaniline. 

Its solubility is poor in common organic solvents and water but readily soluble in dipolar aprotic solvents such as dimethyl formamide (DMF), dimethyl sulfoxide (DMSO) and N-Methyl pyrrolidinone (NMP). It is usually recrystallized from water containing acid. It may also be recrystallized from DMF or NMP [223, 224]. 

BASF AG CRBPII dba DBN DBU DIBAL-H DMAP DMF DMF-DMA DMPU HMDS HMPA HMPT H-LR LDA LDE LRAT MCPBA MOM NMO NMP PCC PhH = Badische Anilin- Soda Fabrik AG = cellular retinol-binding protein type II r dibenzylideneacetone = 1,5-diazabicyclo[4.3.0]non-5-ene = l,8-diazabicyclo[5.4.0]undec-7-ene = diisobutylaluminium hydride = 4-dimethylaminopyridine = A V-dimethylformamide = A,V-dimethylformamide, dimethylacetal = 1,3 -dimethyl-3,4,5,6-tetrahydro-2( 1H)-pyrimidone = hexamethyldisilazane = hexamethylphosphoramide = hexamethylphosphorous triamide = Hoffmann-La Roche = lithium diisopropylamide = lithium diethylamide = lecithin retinol acyltransferase = m-chloroperbenzoic acid = methoxymethyl = iV-methylmorpholine oxide = l-methyl-2-pyrrolidinone = pyridinium chlorochromate = benzene... 

Nucleophilic Substitution Route. Commercial synthesis of poly(arylethersulfone)s is accomplished almost exclusively via the nucleophilic substitution polycondensation route. This synthesis route, discovered at Union Carbide in the eady 1960s (3,4), involves reaction of the bisphenol of choice with 4,4 -dichlorodiphenylsulfone in a dipolar aprotic solvent in the presence of an alkali base. Examples of dipolar aprotic solvents include AT-methyl-2-pyrrolidinone (NMP), dimethyl acetamide (DMAc), sulfolane, and dimethyl sulfoxide (DMSO). Examples of suitable bases are sodium hydroxide, potassium hydroxide, and potassium carbonate. In the case of polysulfone (PSF) synthesis, the reaction is a two-step process in which the dialkali metal salt of bisphenol A (1) is first formed in situ from bisphenol A [80-05-7] by reaction with the base (eg, two molar equivalents of NaOH),... 

Non-deprotonated amides are weak nucleophiles and are only alkylated by trialkyl -oxonium salts or dimethyl sulfate at oxygen or by some carbocations at nitrogen [16, 83]. Alkylation with primary or secondary alkyl halides under basic reaction conditions is usually rather difficult, because of the low nucleophilicity and high basicity of deprotonated amides. Non-cyclic amides are extremely difficult to N-alkylate, and few examples of such reactions (mainly methylations, benzylations, or allyla-tions) have been reported (Scheme 6.21). 4-Halobutyramides, on the other hand, can often be cyclized to pyrrolidinones in high yield by treatment with bases (see Scheme 1.8) [84—86]. 

Butanediol, adipic acid, butyrate, diethyl succinate, dimethyl succinate, maleic anhydride, polyamides, polybutylene succinate, pyrrolidinones, succindiamide, tetrahydrofuran... 

The course of the reductive photocyclization of enamines by irradiation in the presence of sodium borohydride depends on the nature of substituents. Thus the AT-methyl-S-phenyl compound 46 yields a mixture of the pyrrolidinone 47, the piperidinone 48 and the tricyclic compound 49, whereas the dimethyl analogue 50 gives the piperidinone 51 as a mixture of Z- and -isomers. The cyclopentene derivative 52 affords the spiro-pyrrolidinone 53, together with the cyclopentapiperidinone 54, the naphthylthio group being eliminated (Scheme 2)50. 

BENZODIOXOLE, DIMETHYLBENZENE AND 1-METHYL 2-PYRROLIDINONE see BGD088 CYCLOPROPANECARBOXYUC ACID, 2,2-DIMETHYL-3-(2-METHYLPROPENYL)-, ESTER WITH 4-HYDROXY-3-METHYL-2-(2-PROPYNYL)-2-CYCLOPENTEN-l-ONE, trans-(+-)- see THI500 CYCLORYL 21 see SIB600... 

Davies, S. G., Doisneau, G. J. M., Prodger, J. C., Sanganee, H. J. Synthesis of 5-substituted-3,3-dimethyl-2-pyrrolidinones quat chiral auxiliaries. Tetrahedron Lett. 1994, 35, 2369-2372. 

The influence of water as a solvent on the rate of dipolar cycloadditions has been reported [76]. Thus the rate of the 1,3-dipolar cycloaddition of 2,6-dichloroben-zonitrile N-oxide with 2,5-dimethyl-p-benzoquinone in an ethanol/water mixture (60 40) is 14-fold that in chloroform [76b]. Furthermore the use of aqueous solvent facilitates the workup procedure owing to the low solubility of the cycloadduct [76b]. In water-rich solutions, acceleration should be even more important. Thus in water containing 1 mol% of l-cyclohexyl-2-pyrrolidinone an unprecedented increase in the rate of the 1,3-dipolar cycloaddition of phenyl azide to norbornene by a factor of 53 (relative to hexane) is observed [77]. Likewise, the 1,3-dipolar cycloaddition of C,Ar-diphenylnitrone with methyl acrylate is considerably faster in water than in benzene [78]. Similarly, azomethine ylides generated from sarcosine and aqueous formaldehyde can be trapped by dipola-rophiles such as N-ethylmaleimide to provide pyrrolidines in excellent yields... 

Dispersancy Solution copolymers are comparatively easy to produce in dispersant form as copolymerization with an appropriate polar monomer is relatively straightforward. If the polar monomer is also a methacrylate, reactivity ratios are essentially the same and no special procedures are required to produce random copolymers. Commercial examples have included dimethyl (or diethyl)aminoethyl methacrylate [11], hydroxyethyl methacrylate [12] and dimethylamino-ethyl methacrylamide [13]. 2-Methyl-5-vinyl pyridine [14] has also been used commercially, reactivity ratios are such that it copolymerizes slightly faster than alkyl methacrylates. Although composition drift is not severe, it should be added in a programmed fashion if a uniform distribution is desired. V-vinyl pyrrolidinone, in contrast, copolymerizes very sluggishly with methacrylates and is best incorporated via a graft reaction [15], sometimes also grafted in combination with V-vinyl imidazole [16]. Since solution chemistry is used to produce dispersant polymethacrylates, like preparation of the base polymer, only relatively simple process modifications are necessary to produce dispersants commercially. 

It is prepared by treating 2-dimethyl-6-nitrile-3,4-epoxy coumarine first with sodium hydride in dimethylsulphoxide and secondly viith- 2-pyrrolidinone to obtain 2-dimethyl-3-hydroxy-6-nitrile-4 [T (2-pyrrolidinone)] eoumarine. The resolution of the resulting cromakalim is aehieved via the S-a-methylbenzyl carbamate to get the (-)-3S, 4R enantiomer. 

P-Propiolactam, 3,3- and 4,4-disubstituted propiolactams can be polymerized to form unsubstituted and substituted nylon-3. Anionic polymerization was initiated by nylon-6,6 and carried out at 200-250°C. Polymers of high molecular weights were obtained from 3,3-disubstituted lactams. However, solution polymerization at 0-20°C with 25% monomer concentration in a solvent such as dimethyl sulfoxide with strongly basic activators such as potassium pyrrolidinonate also gave high molecular weights. Poly(4,4-dimethylpropiolactam) with Tjinh of 4.5 dl/g and Mw of 50,000 was reported [70]. 

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