Alkylation of 2-Aminothiazoles

Kaye, Irving Allan; Parris, Chester L.

doi:10.1021/ja01131a061

Cited by 7 publications

(8 citation statements)

References 2 publications

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“…The coupler was produced by a known sequence of reactions. 24,28-32 The synthesized dyes were purified by recrystallization and column chro-matography wherever necessary. The melting point of the synthesized dyes were measured on an instrument from Sunder Industrial Products.…”

Section: Methodsmentioning

confidence: 99%

Disperse Dyes Based on 2-N,N-Dibutylamino-4-phenyl thiazole: Synthesis, Solvatochromism, and Dyeing Studies

Shah

Rajeshirke

Nethi

2019

AATCC Journal of Research

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The coupler 2- N, N-dibutylamino-4-phenyl thiazole was used in the preparation of five novel monoazo disperse dyes. Effects of substituents on the electronic absorption properties of the dyes were studied by UV-Vis spectroscopy. The resulting dyes showed little positive solvatochromism, whereas a bathochromic shift in absorption maxima was observed for all five dyes in highly polar solvents. These dyes showed good discharge ability on polyester fabric when compared to nylon fabric and their fastness properties were evaluated. Being low melting, the new dyes could be used for heat transfer printing at a particular set temperature.

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Section: Methodsmentioning

confidence: 99%

Disperse Dyes Based on 2-N,N-Dibutylamino-4-phenyl thiazole: Synthesis, Solvatochromism, and Dyeing Studies

Shah

Rajeshirke

Nethi

2019

AATCC Journal of Research

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“…gives 2-amino-4-methylthiazole (675). CH3 -N sgJcH,C,He 2-Aminothiazole and a number of its A-alkylated derivatives have been alkylated with alkyl, benzyl, and dialkylaminoalkyl halides (483,486,487,490,491). -N…”

Section: Cooc2hsmentioning

confidence: 99%

The Chemistry of the Alkali Amides.

Levine¹,

Fernelius²

1954

Chem. Rev.

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This review of the chemistry of the alkali amides is a continuation of two earlier reviews (17) which have appeared on this subject. In the present review the authors have summarized the work on the inorganic and organic chemistry of the alkali amides which has appeared in the literature from 1937 through 1952. In addition, a considerable amount of previously unpublished material is discussed. Whenever possible, the authors have tried to interpret and evaluate critically the material presented and to call attention to those areas of research which have not been investigated or which should be studied further. Although it has not been convenient to discuss all of the present material under the same headings as were used previously, the changes have not been so extensive as to make cross references difficult.

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“…N-Benzyl-N'-acetylthiourea (VII) (12), m.p. 127.5-129.5°after recrystallization from isopropyl alcohol, was obtained in 95% yield from N-benzylthiourea (7) and acetic anhydride.…”

mentioning

confidence: 99%

“…Method A. To a stirred solution of 27.1 g. (0.143 mole) of 2-benzylaminothiazole (7) in 150 ml. of pyridine and 50 ml.…”

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Acylated 2-Iminothiazolines

Kaye¹,

Parris²

1952

J. Org. Chem.

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Although N, N-disubstituted-2-aminothiazoles may be prepared in good yield by treating secondary 2-thiazolylamines with alkyl or aralkyl halides in the presence of lithium amide (1, 2), only a small amount of 2-benzylaminothiazole was isolated after interaction of 2-aminothiazole with benzyl chloride and lithium amide (1). This reaction was repeated with 2-acetamidothiazole in the expectation that N-benzyl-N-(2-thiazolyl)aeetamide (I; R = methyl) might be formed in better yield, thus offering a superior route, via hydrolytic cleavage of the acyl grouping, for the preparation of 2-benzylaminothiazole. Whereas treatment of the potassium derivative of 2-acetamido-4-methylthiazole with methyl iodide2 (3) and the sodium derivative of 2-formylaminopyridine with alkyl halides (4) have given only extranuclear N-alkylated compounds, our

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Alkylation of 2-Aminothiazoles

Cited by 7 publications

References 2 publications

Disperse Dyes Based on 2-N,N-Dibutylamino-4-phenyl thiazole: Synthesis, Solvatochromism, and Dyeing Studies

Disperse Dyes Based on 2-N,N-Dibutylamino-4-phenyl thiazole: Synthesis, Solvatochromism, and Dyeing Studies

The Chemistry of the Alkali Amides.

Acylated 2-Iminothiazolines

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