14359-97-8

Basic information

• Product Name: 1-hydrazino-3-(methylthio)propan-2-ol
• Synonyms: 1-hydrazino-3-(methylthio)propan-2-ol;1-Hydrazino-3-methylthio-2-propanol;Einecs 238-332-5;1-hydrazinyl-3-(Methylthio)-2-Propanol;1-hydrazinyl-3-(methylthio)propan-2-ol;Nifuratel Impurity 9;2-propanol,1-hydrazinyl-3-(methylthio)
• CAS NO: 14359-97-8
• Molecular Formula: C₄H₁₂N₂OS
• Molecular Weight: 136.21588
• EINECS: 238-332-5
• Mol File: 14359-97-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 339.127 °C at 760 mmHg
• Flash Point: 158.898 °C
• Appearance: /
• Density: 1.146 g/cm³
• Vapor Pressure: 6.3E-06mmHg at 25°C
• Refractive Index: 1.538
• PKA: 13.98±0.20(Predicted)
• CAS DataBase Reference: 1-hydrazino-3-(methylthio)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-hydrazino-3-(methylthio)propan-2-ol(14359-97-8)
• EPA Substance Registry System: 1-hydrazino-3-(methylthio)propan-2-ol(14359-97-8)

Safety Data

• Hazardous Substances Data: 14359-97-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthesis

Add 226.25g hydrazine hydrate to 1000ml reaction flask, heat to 90℃, and add 104.17g of glycidyl ether under stirring. The temperature of the reaction system was controlled at 90℃, and then the excess hydrazine hydrate was concentrated under reduced pressure to obtain 120.10g thick colorless liquid. The purity of the gas phase was 96.8%, namely 1-hydrazino-3-(methylthio)propan-2-ol, and the yield was 88.30%.

InChI:InChI=1/C4H12N2OS/c1-8-3-4(7)2-6-5/h4,6-7H,2-3,5H2,1H3

Upstream product

• 23451-66-3 1-chloro-3-methylsulfanyl-propan-2-ol 
• 45378-62-9 1-methylthio propylene oxide 

Downstream Products

• 25517-72-0 3-amino-5-[(methylthio)methyl]oxazolidin-2-one 

Relevant articles and documents

Preparation method of nifuratel intermediate

The invention provides a preparation method of a nifuratel intermediate. The preparation method comprises the following steps: (1) reacting sodium methyl mercaptide with epoxy chloropropane to prepare 2-(methylthio methyl)-oxetane; (2) dropwise adding 2-(methylthio methyl)-oxetane into hydrazine hydrate to prepare 3-methylthio-2-hydroxy-propyl hydrazine; (3) adding diethyl carbonate into 3-methylthio-2-hydroxy-propyl hydrazine to prepare a nifuratel intermediate, namely N-amino-5-methylthio methyl-2-oxazolidinone; and (4) salifying the prepared N-amino-5-methylthio methyl-2-oxazolidinone and concentrated hydrochloric acid to prepare the nifuratel intermediate hydrochloride. According to the preparation method of the nifuratel intermediate, disclosed by the invention, the nifuratel intermediate can be conveniently and quickly obtained, and the obtained nifuratel intermediate is high in yield, high in purity and stable in quality.

Preparation process of anti-infective drug nifuratel

The invention belongs to the technical field of drug synthesis and in particular relates to a preparation process of an anti-infective drug nifuratel. The preparation process comprises the following steps: taking iodomethane, sodium sulfide and chlorocyclopropane as initial raw materials to obtain epoxy propyl methyl sulfide, carrying out ring-opening reaction with hydrazine hydrate to obtain 3-methylmercapto-2-hydroxyl-propylhydrazine, carrying out a ring-closure reaction to obtain N-amino-5-methylthiomethyl-2-oxazolidinone, hydrolyzing 5-nitro furfural diacetate in the presence of trifluoroacetic acid to obtain 5-nitro-2-furancarboxaldehyde, and performing condensation with N-amino-5-methylthiomethyl-2-oxazolidinone, thereby obtaining the nifuratel. Safe and cheap reagents are selected in the process route, and environment hazards are reduced. Meanwhile, the operating difficulty and reaction after-treatment burdens are reduced, the production safety is ensured, the process is a simple, green and economic process route for preparing the nifuratel, and the obtained product is high in yield, excellent in purity and suitable for large-scale industrial production of the nifuratel.

A method for synthesizing micromolecule

The invention discloses a synthetic method of nifuratel. The synthetic method comprises the steps of carrying out a substitution reaction between epoxy chloropropane and sodium methyl mercaptide in the presence of a phase transfer catalyst to obtain epoxy propyl dimethyl sulfide, and then performing hydrazinolysis, cyclization and condensation on the obtained epoxy propyl dimethyl sulfide to obtain the nifuratel. The synthetic method is high in nifuratel yield, high in purity and low in impurity content; besides the method has the advantages that a ring-closure reaction is carried out under the alkaline condition of sodium methoxide, the use of metal sodium is avoided, production safety is ensured, and simultaneously, the reaction is easy to arouse, easy to control in process, the used raw materials are easy to get, basically no waste liquid is generated in the reaction of each step, and therefore, industrial pollution is greatly reduced; and as a result, the synthetic method of nifuratel is applicable to industrial production.