US3546241A - N-(alkylsulfinyl) ethyl-pyrrolidinones and oxazolidinones - Google Patents
N-(alkylsulfinyl) ethyl-pyrrolidinones and oxazolidinones Download PDFInfo
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- US3546241A US3546241A US730952A US3546241DA US3546241A US 3546241 A US3546241 A US 3546241A US 730952 A US730952 A US 730952A US 3546241D A US3546241D A US 3546241DA US 3546241 A US3546241 A US 3546241A
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- ethyl
- carbon atoms
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- compounds
- pyrrolidinones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07D263/16—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 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon 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
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- R contains 1 to 8 carbons are useful as plasticizers, while those where R contains 8 to 18 carbons are useful as nonionic surfactants.
- the pyrrolidinone derivatives are quite surface active, while the oxazolidinone de rivatives are less surface active, but are foam boosters.
- the instant invention comprises new compounds having the structure wherein R is an alkyl group of 1 to about 18 carbon atoms, R is H or an alkyl group of from 1 to about 6 carbon atoms, X is --O or CH and A is an alkylene group of 2 or 3 carbon atoms.
- compositions are prepared by the oxidation of the corresponding thioether with an oxidizing agent.
- the thioethers can be prepared by the free radical addition of a thiol to the appropriate vinyl or allyl compound, or by the reaction of an N-(2- or 3-haloalkyl-2-pyrrolidinone or -axazolidinone with a thiol in the presence of an alkali metal hydroxide. Both processes are known to those skilled in the art.
- the oxidizing agents that are suitable for making the compounds of this invention include peracids, such as persulfuric, perchromic, peracetic, perbenzoic and monoperphthalic acid; aqueous hydrogen peroxide; and dilute permanganates, such as potassium permanganate and sodium permanganate.
- the ratio of thioether/oxidizing agent should be from a molar equivalent to about a 10% molar excess of the oxidizer. If more than 10 percent excess of the oxidizer is used, some of the thioether is oxidized to the sulfone.
- the reaction should be carried out from about 0 to 100 C., and preferably from about 30 to 60 C. a It is generally desirable to have an inert diluent present to act as a heat sink. Materials such as dioxane, the lower aliphatic ketones and the lower aliphatic alcohols are suitable.
- the compounds of the invention have antimicrobial activity.
- Those in which R contains 1 to 8 carbons, and preferably 1 to 4 carbons, are useful as plasticizers for synthetic resins, such as polyvinyl alcohol, ethyl cellulose, and the like, while those where R contains 8 to 18 carbons are useful as nonionic surfactants.
- the pyrrolidinone derivatives are quite surface active, while the oxazolidinone derivatives are less surface active, but are foam boosters.
- Example 7 Preparation of 3-(3-ethylsulfinyl)propyl- S-methyl-Z-oxazolidinone 8.1 g. (0.043 mole) of 3-(3-ethylthio)propyl-S-methyl- 2-oxazolidinone in 50 ml. of methanol was oxidized as in the above examples with 4.9 g. of 30% aqueous hydrogen peroxide. The resulting product was a viscous orange liquid weighing 8.3 g.
- Example 8 The product of Example 7 was used as a plasticizer for polyvinyl alcohol. 5 g. of the PVA was dissolved in 50 g. of H 0. Eleven grams of this stock solution and 0.25 g. of the above sulfoxide were mixed to give a clear solution. 10 ml. Were cast on a glass plate. After the water evaporated, a tough film remained which retained its flexibility on standing. An identical batch was also cast without the plasticizer. Upon standing for the same length of time, it became quite brittle.
- Droplets of the test organism were applied to the sterile agar, and the plates incubated.
- RSOCH2CI-I2N X wherein R is an alkyl group of 1 to about 18 carbon atoms, R is H or an alkyl group of from 1 to 6 carbon atoms, X is -O or -CH;, and A is an alkylene group of 2 or 3 carbon atoms.
- R is an alkyl group of 10 to 14 carbon atoms and R is H.
Description
United States Patent US. Cl. 260-307 8 Claims ABSTRACT OF THE DISCLOSURE New compounds having the structure wherein R is an alkyl group of 1 to 18 carbon atoms, R is H or an alkyl group of from 1 to 6 carbon atoms, X is -O or -CH and A is an alkylene group of about 2 or 3 carbon atoms.
All these compounds have antimicrobial activity. Those in which R contains 1 to 8 carbons are useful as plasticizers, while those where R contains 8 to 18 carbons are useful as nonionic surfactants. The pyrrolidinone derivatives are quite surface active, while the oxazolidinone de rivatives are less surface active, but are foam boosters.
SUMMARY OF THE INVENTION The instant invention comprises new compounds having the structure wherein R is an alkyl group of 1 to about 18 carbon atoms, R is H or an alkyl group of from 1 to about 6 carbon atoms, X is --O or CH and A is an alkylene group of 2 or 3 carbon atoms.
These compositions are prepared by the oxidation of the corresponding thioether with an oxidizing agent. The thioethers can be prepared by the free radical addition of a thiol to the appropriate vinyl or allyl compound, or by the reaction of an N-(2- or 3-haloalkyl-2-pyrrolidinone or -axazolidinone with a thiol in the presence of an alkali metal hydroxide. Both processes are known to those skilled in the art.
The oxidizing agents that are suitable for making the compounds of this invention include peracids, such as persulfuric, perchromic, peracetic, perbenzoic and monoperphthalic acid; aqueous hydrogen peroxide; and dilute permanganates, such as potassium permanganate and sodium permanganate.
The ratio of thioether/oxidizing agent should be from a molar equivalent to about a 10% molar excess of the oxidizer. If more than 10 percent excess of the oxidizer is used, some of the thioether is oxidized to the sulfone.
The reaction should be carried out from about 0 to 100 C., and preferably from about 30 to 60 C. a It is generally desirable to have an inert diluent present to act as a heat sink. Materials such as dioxane, the lower aliphatic ketones and the lower aliphatic alcohols are suitable.
The compounds of the invention have antimicrobial activity. Those in which R contains 1 to 8 carbons, and preferably 1 to 4 carbons, are useful as plasticizers for synthetic resins, such as polyvinyl alcohol, ethyl cellulose, and the like, while those where R contains 8 to 18 carbons are useful as nonionic surfactants. The pyrrolidinone derivatives are quite surface active, while the oxazolidinone derivatives are less surface active, but are foam boosters.
SPECIFIC EMBODIMENTS The following are specific examples of the method of preparation and use of the new compounds disclosed herein.
Examples 1 to 6 In a typical procedure for preparing the sulfoxides, onehalf mole of the thioether in 200 ml. of methanol is heated to -55 and one-half mole of 30% aqueous hydrogen peroxide is added during about a two-hour period. The mixture is stirred an additional hour and the solvent removed at reduced pressure. The products are white solids quite soluble in alcohol. Typical compounds so prepared are listed in Table I.
TABLE I Example 7.--Preparation of 3-(3-ethylsulfinyl)propyl- S-methyl-Z-oxazolidinone 8.1 g. (0.043 mole) of 3-(3-ethylthio)propyl-S-methyl- 2-oxazolidinone in 50 ml. of methanol was oxidized as in the above examples with 4.9 g. of 30% aqueous hydrogen peroxide. The resulting product was a viscous orange liquid weighing 8.3 g.
Other compounds, such as 3-[(3-pentylsu1finyl)-propyl]-5-hexyl-2-oxazolidinone; 1-[ (2 octadecy1-sulfinyl)- ethyl]-4-propyl-2-pyrrolidinone; 1-[ (2-t-dodecylsulfinyl)- ethyl]-2-pyrrolidinone and 1-[(2-t-octylsulfinyl)-propyl]- Z-pyrrolidinone can be made by oxidizing their thioethers in a similar way.
Example 8 The product of Example 7 was used as a plasticizer for polyvinyl alcohol. 5 g. of the PVA was dissolved in 50 g. of H 0. Eleven grams of this stock solution and 0.25 g. of the above sulfoxide were mixed to give a clear solution. 10 ml. Were cast on a glass plate. After the water evaporated, a tough film remained which retained its flexibility on standing. An identical batch was also cast without the plasticizer. Upon standing for the same length of time, it became quite brittle.
Compounds such as 1-[(Z-pentylsulfinyl)-ethyl]-2-pyrrolidinone, 3- (3-heptylsulfinyl -propyl] -4-ethyl-2-oxazolidinone and 1- [(2 butylsulfinyl)-ethy1]-2-pyrrolidinone are similar in their effects.
Various of the compounds of this invention were tested as antimicrobial agents. The chemicals tested were diluted in a suitable solvent. They were then diluted to the desired concentration in warm melted agar, poured into Petri dishes, and the agar allowed to solidify.
Droplets of the test organism were applied to the sterile agar, and the plates incubated.
The results are given in Table II. The recorded concentrations are the lowest concentrations that prevented growth of the organisms.
TABLE II Microbiological activity of R-SO-CHzCHzN X In vitro microbiological test Compound P.p.m. to give inhibition S. Can Myco Ath. Bart. P Asp. Rhiz.
R X our. alb. phlei. foot suht. pull. terr. 'mg n-Om CH; 500 500 500 500 500 500 500 n-Cn CH; 100 100 500 100 500 500 500 500 n-C 0 500 500 500 500 500 500 500 50 n-C12 o 500 500 500 100 100 100 50 Various of the compounds of this invention were tested We claim: for their surface activity. 1. A compound having the structure Surface tension was determined on 0.1% aqueous solutions with a surface tensiorneter. Interfacial tension Was g I the surface tension between a Nujol mineral oil and a R.SAN x 0.19% aqueous solution. Foam height was determined with a Ross-Miles apparatus, while wetting time was determined on a Draves apparatus. These tests are all well known in the art.
The results are recorded on Table III:
TABLE III Surface activity of RSOCH2CI-I2N X wherein R is an alkyl group of 1 to about 18 carbon atoms, R is H or an alkyl group of from 1 to 6 carbon atoms, X is -O or -CH;, and A is an alkylene group of 2 or 3 carbon atoms.
2. The compound of claim 1 wherein R is an alkyl group of 10 to 14 carbon atoms and R is H.
3. The compound of claim 2 wherein X is CH 4. The compound of claim 1 wherein R is an alkyl group of 1 to 4 carbon atoms.
5. The compound of claim 2 wherein X is O.
6. The compound of claim 4 wherein X is O.
7. The compound of claim 2 wherein A is ethylene.
8. The compound of claim 4 wherein A contains 3 carbon atoms and R is 1.
References Cited UNITED STATES PATENTS 3,438,992 4/1969 Shen et a1. 260--294.8
ALEX MAZEL, Primary Examiner R. V. RUSH, Assistant Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73095268A | 1968-05-21 | 1968-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3546241A true US3546241A (en) | 1970-12-08 |
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ID=24937466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US730952A Expired - Lifetime US3546241A (en) | 1968-05-21 | 1968-05-21 | N-(alkylsulfinyl) ethyl-pyrrolidinones and oxazolidinones |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3546241A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050827A1 (en) * | 1980-10-23 | 1982-05-05 | E.I. Du Pont De Nemours And Company | 3-(p-Alkylsulfonylphenyl)-and 3-(p-alkylsulfinylphenyl)oxazolidinone derivatives as anti-bacterial agents |
| US4450102A (en) * | 1982-11-02 | 1984-05-22 | Phillips Petroleum Company | Sulfur based metal cleaners and corrosion inhibitors |
| US4808644A (en) * | 1984-11-23 | 1989-02-28 | Ciba-Geigy Corporation | Substituted (4-hydroxyphenylthioalkyl) derivatives |
| US6511813B1 (en) | 1999-01-27 | 2003-01-28 | Pharmacia & Upjohn Company | Elongation factor P (EFP) and assays and antimicrobial treatments related to the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3438992A (en) * | 1966-11-09 | 1969-04-15 | Merck & Co Inc | Certain lower-alkyl sulfinylmethyl pyridines |
-
1968
- 1968-05-21 US US730952A patent/US3546241A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3438992A (en) * | 1966-11-09 | 1969-04-15 | Merck & Co Inc | Certain lower-alkyl sulfinylmethyl pyridines |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050827A1 (en) * | 1980-10-23 | 1982-05-05 | E.I. Du Pont De Nemours And Company | 3-(p-Alkylsulfonylphenyl)-and 3-(p-alkylsulfinylphenyl)oxazolidinone derivatives as anti-bacterial agents |
| US4450102A (en) * | 1982-11-02 | 1984-05-22 | Phillips Petroleum Company | Sulfur based metal cleaners and corrosion inhibitors |
| US4808644A (en) * | 1984-11-23 | 1989-02-28 | Ciba-Geigy Corporation | Substituted (4-hydroxyphenylthioalkyl) derivatives |
| US6511813B1 (en) | 1999-01-27 | 2003-01-28 | Pharmacia & Upjohn Company | Elongation factor P (EFP) and assays and antimicrobial treatments related to the same |
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