US3014046A - Quaternary ammonium iodides - Google Patents

Quaternary ammonium iodides Download PDF

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US3014046A
US3014046A US63972A US6397260A US3014046A US 3014046 A US3014046 A US 3014046A US 63972 A US63972 A US 63972A US 6397260 A US6397260 A US 6397260A US 3014046 A US3014046 A US 3014046A
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iodide
ammonium
quaternary ammonium
reaction
compound
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Angelo J Speziale
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/66—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing

Definitions

  • R each represents a-lkyl radicals containing from one to four carhon atoms
  • A represents a cyclic organic structure, such as nited States Patent ()fiice wherein X stands for halogen,.such as chlorine, bromine,
  • alkyl such as methyl, ethyl,. isopropyl, sec-butyl; lower alkoxy, such as methoxy, ethoxy, propox-y, butoxy;
  • n stands for an. integer Zof from 0 to 3;
  • R stands for hydrogen or lower alkyl;
  • W represents a divalent symbol selected from the gr up Consisting of 4 v (3,4-dimetliyl-2-thenylcarbamoylfnethyl) t'rie 'z hyr -O, 'S+-, and -CH and Y represents adivalent chalkogen atom.
  • the preferred chalkogens are oxygen and sulfur.
  • All of the new compounds are quaternary ammonium iodides.
  • which can be synthesized from :alpha-chloroacetyl chloride by first reacting it with a primary or secondary amine containing an organic cyclic nucleus 1 and thereafter replacing the alpha-chlorine'atom with an iodine atom by digesting the product with a watersoluble salt of 'hydro-iodievacid forexample, potassium iodide.
  • the resulting iodoacetamide is then condensed with a tertiary alkyl amine.
  • the first step i.e., the reaction of alpha-chloroacetyl chloride with the amine containing the cyclic nucleus, is carried out by combining stoichiometric equivalent amounts of the two reactants, preferably at reduced temperatuies, e.g., under refrigerated conditions so as to prevent an excessive rate of reaction and in the presence of a stoichiometric amount of sodium hydroxide.
  • the reaction is usually desirable to carry out the reaction in the presence of a'suti'able solvent, such as ethylene dichloride, from which the solid material may be crystallized. If “desired, the composition may be recrystallized from the same or other solvents.
  • a'suti'able solvent such as ethylene dichloride
  • the second reaction involves the reaction at reflux temperatures of the composition obtained above with a water-soluble salt of hydro-iodic acid in the presence of a suitable solvent, such as acetone.
  • a suitable solvent such as acetone.
  • the final reaction involves the addition of the desired tertiary amine to the N-cyclic alpha-iodoacetamide in the Although the reaction proceeds at room temperature, it may be desirable to warm the reaction mixture to temperatures of from about 30 C. to about 100 C. to accelerate the reaction. When the reaction is complete, the solvent is removed by distillation. If desired, the product may be further purified by recrystallizing it from a suitable sol-.
  • vent such as an ethyl acetate-ethanol mixture.
  • N-furfuryl-alpha-iodoacetamide is .then added to .100- rnl. of dry benzene, and 24.4 goof triethylaminein 30 ml. of dry benzene are added over aperiod of minutes.
  • the mixture heated at 60 65 ,C. for 4 hours and then distilled to remove the benzene.
  • the crude ethyl acetate-ethanol mixture to yield 35 g. of triethyl (N-furfurylcarhamoylmethyl) ammonium Tiodide MP.
  • the composition may-
  • the alpha-chloro'-N-( 2-furfuryl) acetsolid residue thus obtained is then-recrystallized from an i Example II.
  • --Tributyl (p-methoxyphenylcarbamoylmethyl) ammonium iodide The procedure of Example I is repeated, except an equimolar amount of p-methoxyaniline is substituted for furfurylamine and an equimolar amount of tributyl amine is substituted for the triethylamine.
  • the resulting compound, tributyl (p-methoxyphenylcarbamoylmethyl) ammonium iodide has a melting point of -101 C.
  • Example III (Cyclohexylcarbamoylmethyl) methyldiethyl ammonium iodide
  • the procedure. of Example I is repeated, except that an equimolar amount of cyclohexylamiue is substituted for the'furfurylamine and an equimolar amount of N- methyldiethylamine is substituted for the triethylamine.
  • the resulting compound, (cyclohexylcarbamoylmethyl) methyldiethyl ammonium iodide hasa melting point of 74-700.
  • the procedure of Example I is repeated,j except that an equimolar amount of thienylarnine is substituted for the furfurylamine and an equimolar amount of trimethylamine is substituted for the triethylamine.
  • the resulting monium iodide is obtained in good yield.
  • the new compounds have biological toxicity and may be used as bacteriostats and as antiseptic agent s. Since they are water-soluble and ionize in contact with water, they are useful cationic emulsion stabilizers especially effective in preserving in aqueous suspension substances subject to bacterial attack. The compounds are also useful in precipitating solids from aqueous colloids, for example, paper pulp, and especially in preventing discoloration by fungal action.
  • R R and R are alkyl radicals containing from 1 to 4 carbon atoms;
  • A is aradical selected from the group consisting of l I l m is an integer of from O to 1 and n is an integer of fiom O to 3. 1 e
  • R R and R are alkyl radicals containing from 1 to 4 carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Patented Dec; 19, 1961 QUA'I'ERNARY AMMONIUM IODIDES Angelo J. Speziale, Creve Coenr, M0., assignor to Montion of'Delaware .;a 'w y v w No Drawing. FiledOct. 21, 1960; Ser. No. 63,972
wh'erein'R 'R and R each represents a-lkyl radicals containing from one to four carhon atoms, A represents a cyclic organic structure, such as nited States Patent ()fiice wherein X stands for halogen,.such as chlorine, bromine,
or iodineglower alkyl, such as methyl, ethyl,. isopropyl, sec-butyl; lower alkoxy, such as methoxy, ethoxy, propox-y, butoxy; n stands for an. integer Zof from 0 to 3; R stands for hydrogen or lower alkyl; W represents a divalent symbol selected from the gr up Consisting of 4 v (3,4-dimetliyl-2-thenylcarbamoylfnethyl) t'rie 'z hyr -O, 'S+-, and -CH and Y represents adivalent chalkogen atom. The preferred chalkogens are oxygen and sulfur.
All of the new compounds are quaternary ammonium iodides. which can be synthesized from :alpha-chloroacetyl chloride by first reacting it with a primary or secondary amine containing an organic cyclic nucleus 1 and thereafter replacing the alpha-chlorine'atom with an iodine atom by digesting the product with a watersoluble salt of 'hydro-iodievacid forexample, potassium iodide. The resulting iodoacetamide is then condensed with a tertiary alkyl amine. These reactions may be represented by the following structuralequations:
-- Representative examplesof monium' iodides of thisinvention inclnde'the following;
.T b yl In the ahoyeequations, the Z symhol represents,
organic structure attached to;theprimary: or secondary amine used in the reaction;
e el aa iat n ii n- -(4-ethylphenylcarbamoylmethyl) trimethyl na il iodide (4,5-dipropyl-2-thieny1carbamoylmethyl) iammonium iodide w(3-chloro-z furfurylcarbamoylmethyl @N etliyldipropyl v ammonium iodide 'N-methyldiethyl (morpholinocarbahioylmethyl) -ium iodide -J -(.ZA-diethoxyphenylearbamoylmethyl) N-propyldihutyl 3 ammonium iodide 2 .(Cyclohexylmethylcarbamoylmethyl) N-ethyldimethyl ammonium iodide Triethyl (piperidinocarbamoyl irethyl) ammonium iodide (N- thy1-3-m h t i n awamqy m fif i b g -N-e thyldipropyl ('thenylcarhamoyhnethyl) ammonium; 25 I iodide I C H (Cyclohexylcarhamo ylmethyl) IN-ethyldimethyl ammonr urn iodide i 7 .i(-2 -to1ylcarbamoylmethy1) ,hl-ethyldimethyl amm nium iodide (2,4-dibromophenylcarbamoylmethyl) triethyl ammonillm iodide t a,-- Triethyl (Z-isobrdpylphenylcatbamoyhnethyl)' ammonium iodide (N- Y b ta rh y a a wy PQ Q Y 'WWW N-propyldibutyl? (a-ptppox phnyicar aindylnietliyljf ammonium iodide ammonium iodide v ethyl ammoniumdodide (4-chloroi ethoxyphe'nylearba Nrmethyldiethylf thi mOr hQIinocarhamoylmethylj -monium iodide a r, 4
nium iodide ,erhylamm niu iodide (-3; chlQro 4ethoxycycloheriylcarbamoyl th monium iodide I (2,4-dichlorocyclohexylmethylcarbamoylniethyl) tri Triet hyl (3 inethylv2 thienylcai liamoylmethylj mmoni um iodide fTrib utyl 3,4-di moi-zan enyia uah yimth91i V nium iodide 'l' ributyl (2,4-dipropoiiyphenylcarhanioylmethyl) amnio- Trimethyl (4-rnethylphenylcarbamoylmetliyli V a rman nium iodide I Triisopropyl(phenylcarbamoylmethyl) 'airiniohiuifi iodide "Tributyl (SrrnethyLZ-furturyIcarbamoylniethyl) Tributyl N-propyl -'2,4-dibromocycloliexylmethylcarr bamoylniethyl) 'ammonium'iodide um iodide (2,4-iodophenylcarbamoylmethyl) -"trimethy1 ammonium iodide iodide Y '(Cyclohexylmetliylcarbamoylmethyll ammonium iodide presence. of asuitable solvent, such as benzene.
;sium,iodide in300 ml. of dry acetone for 3 hours.
,vvashed with dry acetone.
evaporation and there remains 47.5 g. of crude iodo- 1 acetamide.
N-methyldiethyl (thenylcarbamoylmethyl) ammonium iodide N-methyldiethyl (3-propyl-2-furylcarbamoylmethyl) ammonium iodide N-methyldiethyl (N-ethylthienylcarbamoyhnethyl) ammonium iodide The first step, i.e., the reaction of alpha-chloroacetyl chloride with the amine containing the cyclic nucleus, is carried out by combining stoichiometric equivalent amounts of the two reactants, preferably at reduced temperatuies, e.g., under refrigerated conditions so as to prevent an excessive rate of reaction and in the presence of a stoichiometric amount of sodium hydroxide. It
is usually desirable to carry out the reaction in the presence of a'suti'able solvent, such as ethylene dichloride, from which the solid material may be crystallized. If "desired, the composition may be recrystallized from the same or other solvents.
" The second reaction involves the reaction at reflux temperatures of the composition obtained above with a water-soluble salt of hydro-iodic acid in the presence of a suitable solvent, such as acetone. When the reaction is complete, the mixture is cooled to room temperature and the N-cyclic alpha-iodoacetamide is recovered by filtration and drying. be recrystallized from suitable solvents.
The final reaction involves the addition of the desired tertiary amine to the N-cyclic alpha-iodoacetamide in the Although the reaction proceeds at room temperature, it may be desirable to warm the reaction mixture to temperatures of from about 30 C. to about 100 C. to accelerate the reaction. When the reaction is complete, the solvent is removed by distillation. If desired, the product may be further purified by recrystallizing it from a suitable sol-.
vent, such as an ethyl acetate-ethanol mixture.
The following examples are offered in illustration of the invention, but are not to be considered a limitation N thereof.
.Example I.Triethyl (N-furfurylcarbamoylmethyl) ammonium iodide To a suitable reaction vessel is charged 39 g. of furfurylamine, 120 ml. of 20 percent sodium hydroxide sor id'e'is added over a period of onehour and the mixture is stirred for 30 minutes. The organic phase is then separated and washed with water, 5% sodium bicarbonate solution and-watenand dried over anhydrous magnesium sulfate. The ethylene dichloride is removed by vacuum distillation and the resulting product is recrystallized twice from a mixture of water and methanol and once from a benzene solution. amide so obtained is then refluxed with 33.2 g. of potas- The mixture is then cooled to room temperature, filtered, and The. solvent is removed by The crude iodoacetamide is recrystallized from a mixture of '150 ml. Skellysolve B and ,75 ml. of
,ethanol, and 39 g. of the intermediate compound, N furfuryl-alpha-iodoacetamide, are obtained.
The N-furfuryl-alpha-iodoacetamide is .then added to .100- rnl. of dry benzene, and 24.4 goof triethylaminein 30 ml. of dry benzene are added over aperiod of minutes. The mixture heated at 60 65 ,C. for 4 hours and then distilled to remove the benzene. The crude ethyl acetate-ethanol mixture to yield 35 g. of triethyl (N-furfurylcarhamoylmethyl) ammonium Tiodide MP.
If desired, the composition may- The alpha-chloro'-N-( 2-furfuryl) acetsolid residue thus obtained is then-recrystallized from an i Example II.--Tributyl (p-methoxyphenylcarbamoylmethyl) ammonium iodide The procedure of Example I is repeated, except an equimolar amount of p-methoxyaniline is substituted for furfurylamine and an equimolar amount of tributyl amine is substituted for the triethylamine. The resulting compound, tributyl (p-methoxyphenylcarbamoylmethyl) ammonium iodide, has a melting point of -101 C.
Analysis.-Calculatcd: 26.64% I. Found: 26.40% 1.
Example III.(Cyclohexylcarbamoylmethyl) methyldiethyl ammonium iodide The procedure. of Example I is repeated, except that an equimolar amount of cyclohexylamiue is substituted for the'furfurylamine and an equimolar amount of N- methyldiethylamine is substituted for the triethylamine. The resulting compound,, (cyclohexylcarbamoylmethyl) methyldiethyl ammonium iodide, hasa melting point of 74-700.
Analysis-Calculated: 35.8% I. Found: 35.3%;1.
Using the procedure 'of the preceding example, except by utilizing the following primary and secondaryamines (column 1) in place of cyclohexylamine, analogous compounds (column 2) are formed.
Exampl IV.-(3-chloro-2-furfurylcarbamoylmethyl) i ethyldipl'bbJl ammonium iodide i The procedure'of Example I is repeated; except that an equimolar amount of 3-chloro-2-furfurylamine is substituted for the furfurylamine and an equimolar amount of N-ethyldiprop'ylamine is substituted for the triethylamine. The resulting compound (3-chloro-2-furfu rylcarbamoylmethyl). N-ethyldipropyl ammonium iodideyis obtained in good yield. 7 Using the procedure of Example IV, except by utilizing the following primary ,and secondary aminestcolumn 1) in place of 3-chloro-2-furfurylamine, analogous compounds (column 2) are formed.
5-ehloro-2-thenylamlne.
morphollue Example VQ-Trimethyl (thienylcarbanioylmethyl) compound, trimethyl (thienylcarbam'oylmethyl) em ammonium iodide The procedure of Example I is repeated,j except that an equimolar amount of thienylarnine is substituted for the furfurylamine and an equimolar amount of trimethylamine is substituted for the triethylamine. -The resulting monium iodide, is obtained in good yield.
Using the procedure of the preceding examp1e,: except by utilizing the following primary and secondary amines (column 1) in place of thienylamine, analogous compounds (column 2) are formed.
N-methyl-2,5-dlmethy1anlline. Y
5-methyl-2-thenylamine 2-methyI-4-chloroaniline CHa CH;
I o y H II I m-Q-N-C-QHr-Nwmt 1- The new compounds have biological toxicity and may be used as bacteriostats and as antiseptic agent s. Since they are water-soluble and ionize in contact with water, they are useful cationic emulsion stabilizers especially effective in preserving in aqueous suspension substances subject to bacterial attack. The compounds are also useful in precipitating solids from aqueous colloids, for example, paper pulp, and especially in preventing discoloration by fungal action.
The utility of the compounds of this invention in defoliating plants is effectively demonstrated by the data in the following table wherein the activity of triethyl (2,6-dimethylphenylcarbamoylmethyl)ammonium iodide is compared with its chloride and bromide analogs. The experiments were conducted by spraying bean plants with solutions containing varying concentrations of the compounds such that the conceritration data is convertible directly into the indicated pounds per acre rating.
TABLE A Defoliation (Percent) Compound 9 lbsJacre 4 lbs/acre 11 lbs/acre trlethyl-2,6-dimethyl phenyl-carganoylmethyl ammonium loe trlethyl-Q,6-dimethyl phenyl-carbamoylmethyl ammonium bromide trlethyLlfi-dimethyl phenyl-carbfilmoylmethyl ammonium chlor e Percent Percent Percent Nora-The dash mark indicates that this compound was not tested at the indicated rate.
wherein R R and R are alkyl radicals containing from 1 to 4 carbon atoms; A is aradical selected from the group consisting of l I l m is an integer of from O to 1 and n is an integer of fiom O to 3. 1 e
2. A quaternary ammonium compound of the formula NH-C-CH:-NR: I
wherein R R and R are alkyl radicals containing from 1 to 4 carbon atoms.
3. A quaternary ammonium compound of the formula wherein R R and R are alkyl radicals containing'from 1 to 4 carbon atoms, m is an integer of from 0 ml, and Y is a divalent chalkogen atom having an atomic weight of less than 33.
4. A quaternary ammonium compound O LR] cycmmaaomzm] I- \Rz wherein R R and R are alkyl radicals containingfrom 1 to 4 carbon atorns and mis an integer of from 0 to l.
5. A quaternary ammonium compound of the formula of the formula wherein n is an integer of from 0 to 3 and X, R R and R are alkyl radicals having from 1 to 4 carbon atoms.
No references cited.

Claims (2)

1. A QUATERNARY AMMONIUM COMPOUND OF THE FORMULA
6. TRIETHYL (N-FURFURYLCARBAMOYLMETHYL) AMMONIUM IODIDE.
US63972A 1960-10-21 1960-10-21 Quaternary ammonium iodides Expired - Lifetime US3014046A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3168533A (en) * 1962-01-22 1965-02-02 Upjohn Co Carbamoyl derivatives of actinospectacin
US3176025A (en) * 1962-01-22 1965-03-30 Upjohn Co N, n'-bis(lower alkylcarbamoyl)-actinospectinoic acid
US3268577A (en) * 1960-11-15 1966-08-23 Edinburgh Pharmaceutical Ind L Quaternary organic salts of omega-dialkylamino-2, 6-dimethylacetanilides
US3311642A (en) * 1961-10-11 1967-03-28 Monsanto Co Pyranylation of amides
US4015013A (en) * 1972-10-16 1977-03-29 Rhone-Poulenc S.A. Certain quaternary ammonium salts used to control gram-negative bacteria
EP0017946A1 (en) * 1979-04-14 1980-10-29 BASF Aktiengesellschaft Salts of alpha-aminoacetanilides, process for their preparation and their use as plant growth regulators
US4233055A (en) * 1975-12-23 1980-11-11 Ciba-Geigy Corporation Quaternary ammonioalkanecarboxylic acid anilides as plant growth influencing agents
US4552983A (en) * 1982-06-18 1985-11-12 Lonza Ltd. Process for the production of 4-(trialkylammonium)-acetoacetarylides
US4666502A (en) * 1982-02-09 1987-05-19 Sandoz Ltd. Herbicidal N-thienyl-chloroacetamides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3268577A (en) * 1960-11-15 1966-08-23 Edinburgh Pharmaceutical Ind L Quaternary organic salts of omega-dialkylamino-2, 6-dimethylacetanilides
US3311642A (en) * 1961-10-11 1967-03-28 Monsanto Co Pyranylation of amides
US3168533A (en) * 1962-01-22 1965-02-02 Upjohn Co Carbamoyl derivatives of actinospectacin
US3176025A (en) * 1962-01-22 1965-03-30 Upjohn Co N, n'-bis(lower alkylcarbamoyl)-actinospectinoic acid
US4015013A (en) * 1972-10-16 1977-03-29 Rhone-Poulenc S.A. Certain quaternary ammonium salts used to control gram-negative bacteria
US4233055A (en) * 1975-12-23 1980-11-11 Ciba-Geigy Corporation Quaternary ammonioalkanecarboxylic acid anilides as plant growth influencing agents
EP0017946A1 (en) * 1979-04-14 1980-10-29 BASF Aktiengesellschaft Salts of alpha-aminoacetanilides, process for their preparation and their use as plant growth regulators
US4360465A (en) * 1979-04-14 1982-11-23 Basf Aktiengesellschaft N-Allyl pyrrolidinium salt of α-aminoacetanilides
US4666502A (en) * 1982-02-09 1987-05-19 Sandoz Ltd. Herbicidal N-thienyl-chloroacetamides
US4552983A (en) * 1982-06-18 1985-11-12 Lonza Ltd. Process for the production of 4-(trialkylammonium)-acetoacetarylides
US4558158A (en) * 1982-06-18 1985-12-10 Lonza Ltd. Process for the production of 4-(trialkylammonium)-acetoacetarylides

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