255708-80-6

Usage

Uses

Used in Pharmaceutical Research and Development:
255708-80-6 is used as a chiral building block for the synthesis of potential drug candidates in the pharmaceutical industry. Its chiral nature allows for the production of enantiomerically pure compounds, which are essential for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in the Synthesis of Enantiomerically Pure Compounds:
In the field of chiral chemistry, 255708-80-6 is used as a key intermediate for the synthesis of enantiomerically pure compounds. These pure compounds are vital in pharmaceuticals, as they can exhibit different biological activities and potencies compared to their mirror-image counterparts, leading to improved efficacy and reduced side effects.
Used in Drug Design and Optimization:
255708-80-6 serves as a versatile component in drug design and optimization processes. Its unique structural features and reactivity enable the development of novel drug candidates with tailored properties, such as improved pharmacokinetics, selectivity, and potency.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, 255708-80-6 is employed as a valuable tool for exploring the structure-activity relationships of various biologically active compounds. Its incorporation into different molecular frameworks can provide insights into the design of more effective and safer drugs.
Used in Drug Manufacturing Processes:
255708-80-6 is utilized in the manufacturing processes of certain pharmaceuticals, where its unique properties contribute to the production of high-quality, enantiomerically pure drug substances.

Synthetic route

O-methyl-N-nitroisourea (57538-27-9) + methylamine (74-89-5) → N,O-dimethyl-N'-nitroisourea (255708-80-6)

Conditions	Yield
With hydrogenchloride; sodium chloride In water at 40℃; for 6h;	95%

C4H12N2O5S → N,O-dimethyl-N'-nitroisourea (255708-80-6)

Conditions	Yield
With sulfuric acid; nitric acid at 25℃; Concentration;	43.9 g

N,O-dimethyl-N'-nitroisourea (255708-80-6) + (tetrahydro-3-furanyl)methylamine (165253-31-6) → dinetofuran (165252-70-0)

Conditions	Yield
With sodium methylate In methanol at 0 - 65℃; for 4.5h; Temperature; Reagent/catalyst;	99%
With sodium chloride; sodium hydroxide In water at -8 - -5℃; for 10h; Temperature;	90%
With sodium hydroxide In water at 5 - 10℃; for 14h; Product distribution / selectivity;	86%
With sodium hydroxide; sodium chloride In water at -10 - 20℃; for 10 - 23h; Product distribution / selectivity;	81%

N,O-dimethyl-N'-nitroisourea (255708-80-6) + (tetrahydro-3-furanyl)methylamine (165253-31-6) → dinetofuran (165252-70-0) + 2-nitro-1,3-bis(tetrahydro-3-furylmethyl)guanidine (946009-58-1)

Conditions	Yield
With sodium chloride In water at -10 - 10℃; for 23h; Product distribution / selectivity;	A 88% B n/a

N,O-dimethyl-N'-nitroisourea (255708-80-6) + 5-(aminomethyl)-2-chloropyridine (97004-04-1) → 1-((6-chloropyridin-3-yl)methyl)-3-methyl-2-nitroguanidine

Conditions	Yield
With sodium hydroxide; sodium chloride In water at -10 - 20℃; for 10 - 23h; Product distribution / selectivity;	78%

N,O-dimethyl-N'-nitroisourea (255708-80-6) + (tetrahydro-3-furanyl)methylamine (165253-31-6) → 2-nitro-1,3-bis(tetrahydro-3-furylmethyl)guanidine (946009-58-1)

Conditions	Yield
With sodium chloride In water at -10 - 70℃; for 0.18h;	70%

Upstream product

• 57538-27-9 O-methyl-N-nitroisourea 
• 593-51-1 methylamine hydrochloride 
• 57538-27-9 O-methyl-N-nitroisourea 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

A synthetic method of the dinotefuran (by machine translation)

The invention discloses a method for synthesis of dinotefuran, to γ - butyrolactone as raw materials, by Aldol condensation, also the original two-step by the reaction of 3 - hydroxy methyl tetrahydrofuran, then by the Gabriel synthesis of 3 - tetrahydrofuran methyl amine, dimethyl carbonate (DMC) as methylation reagent with the urea synthesis O - methyl isourea, re-nitration synthetic O - methyl - N - nitro-isourea, then with the methylamine reaction synthesis of 1, 3 - dimethyl - 2 - nitro-isourea, final 3 - tetrahydrofuran methylamine with 1, 3 - dimethyl - 2 - nitro-isourea through SN2 Bimolecular nucleophilic substitution reaction, one-step synthesis of dinotefuran. The present invention uses non of dimethyl carbonate as the methylating reagent, the methylation reaction yield ≥ 95%, O - methyl isourea content ≥ 96%, the by-product is carbon dioxide and methanol, process and environmental protection, the overall yield of the dinotefuran ≥ 50%. Synthetic method of this invention to reduce the production cost at the same time, with three wastes, after treatment is simple, the advantages of the environment friendly, and is suitable for industrial production, bring about significant economic benefits. (by machine translation)

N, O - dimethyl - N - nitro-isourea preparation method

The invention discloses a method for preparing N,O-dimethyl-N-nitroisourea by amination reaction, methylation reaction and nitration reaction. The equation is disclosed in the specification. The methyl urea obtained by the amination reaction and the monomethyl sulfate obtained by the methylation reaction can be directly used for the nitration reaction without purification. The cheap and accessible ammonia gas is used as the amination reagent in the amination reaction; in the nitration reaction, the sulfuric acid is used as a catalyst and a reaction solvent, thereby further lowering the raw material cost of the method; and the method has the advantages of mild technological conditions, wide raw material sources, lower production cost, high product quality and high content, and is easy to operate and suitable for industrial production.

IMPROVED METHOD FOR PRODUCING NITROISOUREA DERIVATIVE

Disclosed is an improved process for producing nitroisourea derivatives which is necessary for producing nitroguanidine derivatives having an insecticidal activity. Specifically disclosed is a process for producing nitroisourea derivatives represented by the following general formula (3), which is characterized in that nitroisourea derivatives represented by the following general formula (1) and amines represented by the following general formula (2) or a salt thereof are reacted in the presence of a catalytic amount of a hydrogen carbonate,