Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
  • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
  • C07D241/52—Oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
  • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
  • C07D241/40—Benzopyrazines
  • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Definitions

• oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide.
• the present invention discloses a process for the preparation of methyl 3-( 2-quinoxalinylmethylene)carbazate N ,N -dioxide which comprises contacting methyl 3-(2-quinoxalinylmethylene)carbazate with at least about 2 equivalents of oxidizing agent in a reaction inert solvent at a temperature of from about C. up to 100C. until the reaction is substantially complete, said oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, mchloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide, and recovery of the product.
• a catalyst is usually employed.
• Suitable catalysts are tungstic acid, sodium tungstate, sodium vanadate, sodium molybdate, potassium tungstate, potassium molybdate, vanadium pentaoxide, zirconium dioxide, tungsten trioxide or molybdenum trioxide.
• a particularly preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is peracetic acid and said solvent is acetic acid, since both the reagent and solvent are inexpensive.
• a second preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is m-chloroperbenzoic acid and said solvent is chloroform.
• reaction tem perature is preferably maintained at less than 50C.
• the new reaction of the present invention is carried out in a reaction-inert solvent.
• An inert solvent for purposes of this invention contemplates any solvent which allows solubilization of the reactants and is free of ad.- verse effect on the reagents and products under the conditions employed.
• Two preferred types include organic acids, such as acetic acid, and halogenated solvents, such as chloroform and methylene chloride. In some cases water may be employed. However, any solvent possessing the qualities set forth above will be satisfactory.
• the temperature at which the reaction is performed may vary from C. to about 100C. and for the most part the optimum temperature will vary with the choice of oxidizing agent. Depending upon the particular oxidizing agent and temperature, the reaction time can vary from a few minutes to as long as 24 hours. Generally, to ensure complete reaction the relatively long time periods are preferred. Optimum reaction conditions are readily determined by experiment.
• the proportion of oxidizing agent relative to the starting carbazate may vary widely butfor efficient conversion at least about two equivalents of oxidizing agent per mole ofcarbanate are preferred.
• the product is a crystalline substance which precipitates from the reaction mixture. It is collected by suit- .able means and dried.
• the valuable product of this invention exhibits activity as urinary tract systemic anti-infective in animals, includingman, against a wide :variety of microorganisms including Gram positive and Gram-negative bacteria. It is especially valuable against Gram negative infection both invitro and in vivo.
• poultry chickens, ducks, turkeys
• the beneficial effects in growth rate and feed efficiency are over and above what is normally obtained with complete nutritious diets containing all the nutrients, vitamins, minerals and other factors known to be required for the maximum healthy growth of such animals.
• the animals thus attain market size sooner and on less feed.
• feed compositions have been found to be particularly valuable and outstanding in the case of such animals as poultry, rats, hogs, swine, lambs, cattle, and the like. In some instances the degree of response may vary with respect to the sex of the animals.
• the products may, of course, be administered in one component of the feed or they may be blended uniformly throughout a mixed feed; alternatively as noted above, they may be administered in an equivalent amount via the animalss water ration. It should be noted that a variety of feed components may be of use in the nutritionally balanced feeds.
• reaction mixture is allowed to stand for 12 hours and then diluted with water.
• the solid which precipitates is collected, washed with water and dried to give crystalline methyl 3-(2-quinoxalinylmethylene)carbazate N ,N -dioxide.
• EXAMPLE lll A mixture of methyl 3-( 2-quinoxalinylmethylene)- carbazate (23.0 g, 0.1 mole), tungstic acid (2.5 g) and 30 ml of t-butanol is heated to 6065. An aqueous solution of 30 percent hydrogen peroxide (30 ml) is solvent is acetic acid.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Luminescent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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Citations (5)

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• 1973
  • 1973-03-07 US US338906A patent/US3926991A/en not_active Expired - Lifetime
• 1974
  • 1974-02-04 IE IE197/74A patent/IE39170B1/xx unknown
  • 1974-02-05 SE SE7401528A patent/SE420603B/xx not_active IP Right Cessation
  • 1974-02-05 ZA ZA740745A patent/ZA74745B/xx unknown
  • 1974-02-13 NL NL7401966A patent/NL7401966A/xx unknown
  • 1974-02-20 FI FI490/74A patent/FI59404C/fi active
  • 1974-02-20 IT IT48504/74A patent/IT1056054B/it active
  • 1974-02-20 YU YU00439/74A patent/YU39150B/xx unknown
  • 1974-02-21 JP JP49019992A patent/JPS5024282A/ja active Pending
  • 1974-02-21 DK DK92574AA patent/DK138945B/da not_active IP Right Cessation
  • 1974-02-21 ES ES423464A patent/ES423464A1/es not_active Expired
  • 1974-02-22 FR FR7406155A patent/FR2220524B1/fr not_active Expired
  • 1974-02-22 AR AR252487A patent/AR200516A1/es active
  • 1974-02-22 CH CH254874A patent/CH580096A5/xx not_active IP Right Cessation
  • 1974-02-22 LU LU69471A patent/LU69471A1/xx unknown
  • 1974-02-28 HU HUPI408A patent/HU170488B/hu unknown
  • 1974-02-28 CS CS7400001493A patent/CS180003B2/cs unknown
  • 1974-03-01 SU SU2002363A patent/SU539527A3/ru active
  • 1974-03-01 PL PL1974169209A patent/PL94858B1/pl unknown
  • 1974-03-05 CA CA194,053A patent/CA982584A/en not_active Expired
  • 1974-03-06 GB GB1014974A patent/GB1459561A/en not_active Expired
• 1977
  • 1977-09-15 HK HK471/77A patent/HK47177A/xx unknown
• 1978
  • 1978-12-30 MY MY13/78A patent/MY7800013A/xx unknown

Patent Citations (5)

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