US3354171A - Nitroazoline compounds and process therefor - Google Patents

Nitroazoline compounds and process therefor Download PDF

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US3354171A
US3354171A US488776A US48877665A US3354171A US 3354171 A US3354171 A US 3354171A US 488776 A US488776 A US 488776A US 48877665 A US48877665 A US 48877665A US 3354171 A US3354171 A US 3354171A
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nitro
alkyl
oxazoline
carbon atoms
azoline
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Herbert L Wehrmeister
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Commercial Solvents Corp
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Commercial Solvents Corp
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Priority to FR73687A priority patent/FR1490135A/fr
Priority to BE685951D priority patent/BE685951A/xx
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms

Definitions

  • This invention generally relates to new nitroazoline compounds.
  • it relates to new nitrooxazoline and nitroimidazoline compositions and process for the production thereof.
  • it relates to 2-(nitroalkyD-Z-azolines including aryl-, alkyl-, and alkenylsubstituted nitroalkyl azolines.
  • it relates to the nitroazoline compounds 2- 3-nitro-3 -alkyl) -2-oxazolines,
  • X is either the oxygen of the oxazoline ring, or it is the imide nitrogen of the imidazoline ring. It is conventional nomenclature to assign to X the position 1 and to number the remaining constituents of the ring in numerical sequence in a direction which will give the N the lowest number, i.e. in a counter-clockwise direction in the above formula. Thus the carbon atom between X and N is position 2, N is 3, etc. A carbon atom attached to the carbon atom in the 2-position is referred to in this specification as the alpha carbon atom.
  • a third object of this invention is to provide 2-(1-alkyl- 3-nitroalkyl)-2-oxazolines.
  • a fourth object of this invention is to provide 2-(1- ary1alkyl-3 -nitroalkyl) -2-oxazolines.
  • a fifth object of this invention is to provide 2-(1- alkenyl-3-nitroalkyl -2-oxazo1ines.
  • a sixth object of this invention is to provide 2-(laryl-3-nitroalkyl -2-oxazolines.
  • a seventh object of this invention is to provide 2-(3- nitro-3 -alkyl) -2-imidazolines.
  • Another object of this invention is to provide 2-(1- alkyl-3 -nitroalkyl -2-imidazolines.
  • a further object of this invention is to provide 2-(1- arylalkyl-3 -nitroalkyl -2-imidazolines.
  • a still further object of this invention is to provide 2-( 1-alkenyl-3-nitroalkyl)-2-imidazolines.
  • Still yet another object of this invention is to provide 2- 1-aryl-3-nitroalkyl)-2-imidazo1ines.
  • oxazolines and imidazolines are represented by the following general where Y can be an alkyl radical, aryl radical, arylalkyl, or hydroxyalkyl radical; R is hydrogen, alkyl, alkenyl, aryl or arylalkyl radical of from 1 to about 20 carbon atoms; R and R, can be hydrogen, alkyl radicals having from 1 to 3 carbon atoms, hydroxymethyl or the group acyloxy methyl, with the proviso that when X is R and R, can be hydrogen or alkyl radicals of from 1 to 3 carbon atoms. R and R can be the same or they can be different.
  • compositions of this invention can be prepared by reacting about 1 mole of a secondary nitroalkane in the presence of a condensationcatalyst with about 1 mole of a Z-ethenyl azoline having the general formula:
  • the compound prepared is a 2-(l-aryl-3-nitroalkyl)-2-oxazoline.
  • the compound prepared is a 2-(1-ary1- alkyl-3-nitroalkyl)-2-imidazoline.
  • the compound prepared is a 2-(1- alkenyl-S-nitroalkyl)-2-imidazoline.
  • the compound prepared is a 2-(l-aryl-3- nitroalkyl -2-imid azoline.
  • the reaction is conducted by charging the reactants and catalyst into a suitable reaction vessel equipped with a reflux condenser and an agitator.
  • a solvent can be used if desired and generally a solvent is preferred.
  • the amount of catalyst used is preferably from about 0.5% to about 5% by weight based on the weight of the azoline, i.e. the oxazoline or imidazoline. Heat is applied from a heat source and the mixture is reacted at reflux temperature until the nitroalkane is consumed. When nitroalkane is no longer condensing at the top of the reflux column, and the pot temperature has risen to at least C., the reaction is substantially complete.
  • the entire product of the reaction can be used if desired, but usually it is preferred to purify it. Any known method of purification, such as extraction or distillation can be used.
  • Distillation is a preferred method for compounds having suflicient thermal stability.
  • the reaction product is distilled at a reduced pressure of from about 10 to about 15 mm., and the heads and tails are discarded. If still further refinement is preferred, the distilled crude is fractionated at a pressure of from about 1 to about 5 mm.
  • the temperature at which these distillations occur will usually be less than 200 C. and will vary according to the ethenyl azoline used as the starting material as Well as the pressure at which the distillation is conducted. In general, if R is a long chain radical, the temperature tends to be higher than if R is a short chain radical.
  • the ethenyl azoline is prepared in situ and is then reacted with the nitroalkane to form the nitro derivative.
  • One method is to react about 1 mole of a 2-substituted azoline, e.g. a 2- alkyl azoline, a 2-alkenyl azoline, or a Z-arylalkyl azoline with about 1 mole of a 1-hydroxy-2-alkyl-2-nitroalkane, e.g. 2-nitro-2-methyl-l-propanol, preferably in the presence of a condensation catalyst. This reaction releases about 1 mole of water, which must be removed from the reaction mixture before the reaction is complete.
  • a 2-substituted azoline e.g. a 2- alkyl azoline, a 2-alkenyl azoline, or a Z-arylalkyl azoline
  • a 1-hydroxy-2-alkyl-2-nitroalkane e.g. 2-nitro-2-methyl-l-
  • the reaction is conveniently conducted in the presence of a water-entraining solvent at reflux temperatures and at arnbient pressures. The heating is continued until water of reaction is no longer being released as can be determined by use of a water separator at the top of the reflux column.
  • the water-entraining solvent such as hexane, octane, benzene, toluene, xylene, 2-nitropropane, etc., reduces the viscosity of the reaction mixture and removes azeotropically the Water of reaction. After removal of water and water-entraining solvent by distillation, the entire product of the reaction can be used if desired but usually it is preferred to purify it.
  • the preferred embodiment of this invention is to prepare the ethenyl azoline in situ by condensing a Z-su-bstituted azoline with formaldehyde from a formaldehyde source and reacting the resulting product with a secondary nitroalkane, preferably in the presence of a condensation catalyst.
  • This embodiment is preferred to the two described previously because of the lower costs of the reactants.
  • the reaction releases 1 mole of Water and in general is conducted in the same manner as the one just described.
  • the nitroalkane can be introduced to the reaction vessel at the start of the reaction as in Example 2, or it can be added later after the reaction of formaldehyde with the azoline is complete as in Example 14.
  • nitro-azolines will be referred to as nitro-oxazolines and nitro-imidazolines.
  • nitro-oxazolines and nitro-imidazolines of this invention are useful as plasticizers for nitrocellulose and as intermediates for the preparation of amino-oxaz-olines and amino-imidazolines.
  • nitro-oxazolines and nitro-imidazolines of this invention are employed as plasticizers in nitrocellulose lacquers in the same manner as is used for other such plasticizers as is known to those skilled in the art.
  • these nitro-oxazolines and nitro-imidazolines are employed in conventional lacquers in an amount of [from about 75% to about 125% by weight of the weight of the nitrocellulose.
  • Amino-oxazolines and amino-irnidazolines can be prepared from the nitro-oxazolines and nitro-imidazolines of this invention by hydrogenation in the presence of a hydrogenation catalyst, e.g. Raney nickel at about 1000 p.s.i.g. at about 30 C. in accordance with procedures known in the art. However, if R R or R contain unsaturated linkages, they will probably be hydrogenated in the presence of Raney nickel.
  • a hydrogenation catalyst e.g. Raney nickel at about 1000 p.s.i.g. at about 30 C.
  • Azolines useful for the preparation of the nit-nooxazolines and nitro-imidazolines in the practice of this invention can be obtained commercially or they can be prepared.
  • Commercially available 2-substituted oxazolines and 2-substituted imidazolines having an alkyl, arylal'kyl or alkenyl radical in the 2-position are satisfactory for the practice of this invention.
  • Several methods of preparation of 2-substit-uted oxazolines and 2-substituted imidazolines are known in the art, and any method giving an alkyl, alkenyl, or arylalkyl radical in the 2-position will give oxazolines and imidazolines satisfactory for the practice of this invention.
  • Oxazolines substituted in the 4- and 5-positions and imidazolines substituted in the 1-, 4-, and 5-positions are also satisfactory provided they have an alkyl, alkenyl, or arylalkyl radical on the 2-position.
  • One procedure which has given satisfactory results for preparing such compounds is given by H. L. Wehrmeister, J. Org. Chem. 26, 3821 (1961).
  • the ethenyl azolines employed in the practice of this invention are readily prepared from 2-alkyl oxazolines, 2-arylalkyl oxazolines, 2-alkenyl oxazolines, 2-alkyl imidazolines, '2-arylalkyl imidazolines, and 2-alkenyl imidazolines by treating them with a formaldehyde source such as formaldehyde or paraformaldehyde as is known by those skilled in the art and as described in Example 14. Also, a satisfactory procedure is given by H. L. Wehrmeister, J. Org. Chem. 27, 4418 (1962).
  • Z-substituted oxazolines can be readily prepared by reacting an aliphatic or aromatic monocarboxylic acid having 2 or more carbon atoms with an alkanolamine having the following general structure:
  • R and R are alkyl radicals of from 1 to 3 carbon atoms or hydroxymethyl.
  • R and R can be the same or they can be different.
  • alkanolamines include but are not limited to 2-amino-2-methyl-l-propanol; 2-amino- 2 methyl-1,3-propanediol; Z-amino-Z-ethyl-1,3-propanediol; Z-amino-2-hydroxymethyl-1,3-propanediol.
  • R or R or both are hydroxyalkyl
  • the resulting hydroxyoxazoline can be esterified with aliphatic or aromatic monocarboxylic acids according to methods known in the art and these oxazoline esters are also useful in the practice of this invention.
  • R is alkyl
  • R is alkenyl
  • R is arylalkyl or aryl, i.e. if the monocarboxylic acid is phenyl acetic acid, R is aryl.
  • both R and R will be hydroxymethyl if 1 mole of a monocarboxylic acid is used to form the oxazoline.
  • These hydroxymethyl groups can then he esterified by an aliphatic, an aromatic or an aryl alkyl monocarboxylic acid to form acyloxymethyl groups.
  • Either the same acid used to form the oxazoline can be employed, or a different one can be used.
  • it is preferred that the hydroxymethyl group be esterified with the same acid used to form the oxazoline it is convenient to react the alkanolamine with 3 moles of acid whereupon the di-ester oxazoline is formed in a single step.
  • R or R is hydroxymethyl and the other is an alkyl group of from 1 to 3 carbon atoms.
  • the hydroxymethyl group can similarly be esterified, either at the time of oxazoline formation by the use of 2 moles of acid, or in a separate step.
  • 2-alkyl or 2-alkenyl imidazolines can be readily prepared from a monocarboxylic acid having 2 or more carbon atoms by reacting it with a diamine having the following general formula:
  • R and R are hydrogen or alkyl radicals of from 1 to 3 carbon atoms.
  • R and R can be the same or they can be different.
  • Y is lower alkyl, aryl, arylalkyl or hydroxyalkyl.
  • diamines include but are not limited to N -isopr0pyl-2-methyl-l,2-propanediamine; N -phenyl- 2 methyl 1,2-propanediamine; N -(2-hydroxyethyl)-2- methyl 1,2-propanediamine; N-(2-aminoisobutyl)butylamine; and N-(2-aminoisobutyl)benzylamine.
  • the monocar'boxylic acids which can be used to form the oxazolines, imidazolines and their esters can be represented by the formula R CH COOH where R can be hydrogen, alkyl, arylalkyl, alkenyl or aryl radical of from 1 to about 20 carbon atoms.
  • R can be hydrogen, alkyl, arylalkyl, alkenyl or aryl radical of from 1 to about 20 carbon atoms.
  • These acids are the saturated and unsaturated acids of the fatty acid series, including phenyl substituted fatty acids, beginning with acetic acid.
  • acids examples include but are not limited to acetic, phenylacetic propionic, phenylpropionic caproic, coconut oil fatty acids, tall oil fatty acids, oleic acid, stearic acid, fish oil acids, and the like. Also mixtures of these acids can be employed in preparing these oxazolines and imidazolines.
  • the nitroalkanes used in the practice of this invention are secondary nitroalkanes having from 3 to 6 carbon atoms in the molecule, including but not limited to 2- nit-ropropane, 2-nitrobutane, nitrocyclohexane, and preferably 2-nitropropane.
  • the monohydroxy nitroalkanes used in the practice of this invention' are those having from 4 to 6 carbon atoms in the molecule and having the nitro group and an alkyl group in the 2-position, preferably 2-nitro-2-methyl-l-propanol.
  • the commercial grade materials are fully satisfactory for the practice of 1 this invention.
  • the quantity of catalyst chosen for this example was greater than that in Example 1 to reduce the reaction period.
  • the 2-nitropropane acted as the water-entraining solvent until it was substantially consumed by reaction.
  • the flask was equipped with a sealed stirrer and thermometer and was attached to an 18" Vigreux column equipped with a water separator and a reflux condenser. The mixture was heated at reflux for about 9 hours during which time the temperature rose to about 152 C.
  • the pot residue was flash distilled and a cut boiling 10 at 106 C. to 125 C. at 1.5-2.5 mm. was fractionated through an 18" Vigreux column. A relatively pure cut boiling at 90-110 C. at 1.5 mm. was taken as the principal product.
  • Example 3 Example 2 is repeated except that 2-isopropenyl-4,4-dimethyl-Z-oxazoline is used in place of 2-ethyl-4,4- dirnethyl 2- oxazoline and the paraformaldehyde is omitted.
  • the pot residue was flash distilled through an 18" Vigreux column and a cut boiling at 93-113 C. at 0.8 mm. was taken. This cut was fractionated through an 18" Vigreux column and a cut was taken at -94 C. and
  • Example 24 The preparation of 2 (3-nitro-l,3-dimethylbutyl)-1- isopropyl 4,4 dimethyl-Z-imidazoline was conducted as follows:
  • R is selected from Yl I- R and R are selected from hydrogen and alkyl radicals of from 1 to 3 carbon atoms.
  • nitro-oxazoline compounds represented by the an 18 Vigreux column. A relatively pure cut was made followin Structural form ula. at MM? 0. and at 0.3 mm. g
  • nitro-imidazoline produced in the above reaction is incorporated in a nitrocellulose lacquer as the plasticizer H2C-CR2 therefor in an amount about equal to the weight of the 0 1; nitrocellulose.
  • a durable, flexible film is formed when 20 CH the lacquer is applied to the surface of an object and al- I lowed to dry.
  • H-CIICHTCCH3 Example R1 N02 The experiment of Example 24 is repeated except that wherein R is selected from the group consisting of hydro- 2-nitro-2-methyl-l-propanol is used in place of para- 25 gen and alkyl, arylalkyl, :alkenyl, and aryl radicals havformaldehyde and 2-nitropropane.
  • R and R are selected from the group consist- 1.
  • X is selected from the group consisting of --O-- and wherein Y is selected from the group consisting of hydrogen and lower alkyl, aryl, arylialkyl and hydroxyalkyl atoms, hydroxymethyl radical, and the acyloxymethyl group, said acyl group being an aliphatic, aromatic or aralkyl monocarboxylic acyl group of from 2 to 22 carbon atoms.
  • R is an alkyl radical having from 1 to carbon atoms and R and R are selected from the group consisting of hydrogen, alkyl radicals having from 1 to 3 carbon atoms, hydroxymethyl radical, and the acyloxymethyl group, said acyl group being an aliphatic, aromatic or aralkyl monocar-boxylic acyl group of from 2 to 22 carbon atoms.
  • R is an aryl alkyl radical corresponding to the formula where x is an integer of from 1 to 14 and R and R are selected from the group consisting of hydrogen, alkyl radicals having from 1 to 3 carbon atoms, hydroxy methyl radicals and the acyloxymethyl group, said acyl group being an aliphatic, laromatic or aralkyl monocarboxylic acyl group having from 2 to 22 carbon atoms.
  • R is an .alkenyl radical having from 2 to 20 carbon atoms and R and R are selected from the group consisting of hydrogen, alkyl radicals having from 1 to 3 carbon atoms, hydroxymethyl radical, and the acyloxymethyl group, said acyl group being an aliphatic, aromatic or aralkyl monocarboxylic acyl group of from 2 to 22 carbon atoms.
  • R is the phenyl radical and R and R are selected from the group consisting of hydrogen, alkyl radicals having from 1 to 3 carbon atoms, hydroxymethyl radicals, and acyloxymethyl group, said acyl group being an aliphatic, aromatic or aralkyl monocarboxylic acyl group of from 2 to 22 carbon atoms.
  • Y is selected from the group consisting of lower alkyl, aryl, arylalkyl, and hydroxyalkyl radicals of from 1 to 7 carbon atoms
  • R is selected from the group consisting of hydrogen and alkyl, arylalkyl, alkenyl, and aryl radicals having from 1 to 20 carbon atoms
  • R and R are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms.
  • Y is selected from the group consisting of lower alkyl, aryl, arylalkyl and hydroxyalkyl radicals of from 1 to 7 carbon atoms; and R and R are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms.
  • R is arylalkyl radical corresponding to the formula where x is an integer of from 1 to 14; Y is selected from the group consisting of alkyl, aryl, arylalkyl, and hydroxyalkyl radicals of from 1 to 7 carbon atoms; and R and R are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms.
  • R is an alkenyl radical having from 2 to 20 carbon atoms
  • Y is selected from the group consisting of alkyl, aryl, arylalkyl, and hydroxyalkyl radicals of from 1 to 7 carbon atoms
  • R and R are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms.
  • R is the phenyl radical
  • Y is selected from the group consisting lower alkyl, aryl, arylalkyl, and hydroxyalkyl radicals
  • R and R are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms.
  • a process for the production of a nitro azoline comprising the steps of:
  • X is selected from the group O and consisting of R and R are selected from hydrogen and alkyl radicals of from 1 to 3 carbon atoms,
  • a process for the production of a nitroazoline comprising the steps of (a) preparing a mixture of a 1-hydroxy-2-alkyl-2- nitroalkane and a 2-substituted-2-azoline at a mole ratio of about 1:1 in the presence of an inert solvent and from about 0.5% to about 5% by weight, based on the Weight of said 2-substituted-2-azoline, of an acidic condensation catalyst,
  • a process for the production of a nitro-azoline comprising the steps of:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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US488776A 1965-09-20 1965-09-20 Nitroazoline compounds and process therefor Expired - Lifetime US3354171A (en)

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US488776A US3354171A (en) 1965-09-20 1965-09-20 Nitroazoline compounds and process therefor
GB24642/66A GB1135093A (en) 1965-09-20 1966-06-02 Nitroazoline compounds and their preparation
DE1966C0039462 DE1670356B2 (de) 1965-09-20 1966-06-28 Verfahren zur herstellung von 2-nitroalkyloxazolinen oder -imidazolinen
FR73687A FR1490135A (fr) 1965-09-20 1966-08-22 Composés de la nitro-azoline et procédé pour leur préparation
BE685951D BE685951A (cs) 1965-09-20 1966-08-24

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3948934A (en) * 1973-11-01 1976-04-06 Shell Oil Company 2-(Nitromethylene)-1,3-diazacycloalkane insect control agents
US3996372A (en) * 1975-12-03 1976-12-07 Shell Oil Company Insecticidal 1-acyl-3-substituted-2-(nitro(phenylthio)-methylene)imidazolidines

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248397A (en) * 1964-12-04 1966-04-26 Commercial Solvents Corp Process for bodying oxazoline drying oils and product thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248397A (en) * 1964-12-04 1966-04-26 Commercial Solvents Corp Process for bodying oxazoline drying oils and product thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3948934A (en) * 1973-11-01 1976-04-06 Shell Oil Company 2-(Nitromethylene)-1,3-diazacycloalkane insect control agents
US3996372A (en) * 1975-12-03 1976-12-07 Shell Oil Company Insecticidal 1-acyl-3-substituted-2-(nitro(phenylthio)-methylene)imidazolidines

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GB1135093A (en) 1968-11-27
DE1670356B2 (de) 1976-08-19
BE685951A (cs) 1967-02-01

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