A study of the preparation of pyrazole and its derivatives by the interaction of epichlorohydrin and hydrazines, and a study of their properties

Godfrey, Keith Ernest (1954) A study of the preparation of pyrazole and its derivatives by the interaction of epichlorohydrin and hydrazines, and a study of their properties. Doctoral thesis, Northern Polytechnic.

Abstract

1. The preparation of 1-phenylpyrazole from phenylhydrazine and epichlorohydrin has been considerably improved; this method affords the best route to this compound. A possible reaction sequence in this synthesis is discussed, and evidence is offered to support it. 2. The reaction of epichlorohydrin with hydrazine and substituted hydrazines has been studied, and a new method for the synthesis of 1-(nitrophenyl)-pyrazoles has been introduced. 3. Some substitution reactions of l-phenylpyrazole, such as chloromethylation, mercuration, and thiocyanation, have been examined, and various reactions of the products have been studied. A number of hitherto unknown 4-substituted 1-phenylpyrazoles have thus been prepared, and improved methods obtained for previously known compounds, 4. The following new compounds have been pre pared and characterised. 1—(m-Tolyl)—pyrazole. 4-Bromo-l-(p-tolyl)-pyrazole. 4-Hydroxy-1-(p-tolyl)-pyrazolidine . l-(m-Nitrophenyl)-pyrazole. 4-Chloromethyl-l-phenylpyrazole. Di-(l-phenyl-4-pyrazolyl)-methane. Di-(l-phenyl-4-pyrazolyl)-ethane. Di-(l-phenyl-4-pyrazolyl) ketone. Di-(l-phenyl-4-pyrazolyl) ketoxime. Di-(l-phenyl-4-pyrazolylmethyl) ether. 4-acetoxymethyl-l-phenylpyrazole. 1- Phenyl -4 -propoxymethylpyrazole. 4-Hydroxymethyl-l-phenylpyrazole. 4- (p-Nitrobenzoyloxymethyl) -1-phenylpyrazole. 1-Phenylpyrazole -4-aldehyde. 1- Phenylpyrazole -4-aldoxime. 1-Phenyl-4-pyrazolylmethyleneacetone. Di-(l-phenyl-4-pyrazolylmethylene )-acetone . -(l-Phenyl-4-pyrazolyl)-acrylic acid. 2 - Phenyl-4-(l-phenyl-4-pyrazolylmethylene)-oxazol-5-one. 2-Methyl-4-(l-phenyl-4 -pyrazolylmethylene ) -oxazol-5-one . α-Amino- -(l-phenyl-4 -pyrazolyl)-propionic acid. 1-Phenyl-4 -pyrazolylmethyleneaniline. 4-Acetoxymercuri-l-phenylpyrazole. 4-Chloromercuri-l-phenylpyrazole. l-Phenyl-4-thiocyanopyrazole. 4-(S-Benzylthio)-l-phenylpyrazole.

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