GB1135093A - Nitroazoline compounds and their preparation - Google Patents
Nitroazoline compounds and their preparationInfo
- Publication number
- GB1135093A GB1135093A GB24642/66A GB2464266A GB1135093A GB 1135093 A GB1135093 A GB 1135093A GB 24642/66 A GB24642/66 A GB 24642/66A GB 2464266 A GB2464266 A GB 2464266A GB 1135093 A GB1135093 A GB 1135093A
- Authority
- GB
- United Kingdom
- Prior art keywords
- azoline
- mol
- hydrogen
- heating
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- 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
Landscapes
- 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)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,135,093. Nitro-azolines. COMMERCIAL SOLVENTS CORP. 2 June, 1966 [20 Sept., 1965], No. 24642/66. Heading C2C. [Also in Division C3] The invention comprises oxazolines and imidazolines of the formula wherein X is -O- or Y-N-, where Y is hydrogen or a C 1-5 alkyl, C 1-3 hydroxyalkyl or a phenyl or benzyl radical; R 1 is hydrogen or an alkyl, alkenyl, aryl or aralkyl group containing 1-20 carbon atoms; R 2 and R 3 are the same or different and represent hydrogen or a C 1-3 alkyl or hydroxy methyl group or an acyloxymethyl -CH 2 O.CO.CH 2 R 1 with the proviso that when X is Y-N-, R 2 and R 3 are hydrogen or C 1-3 alkyl groups. The compounds can be prepared by reacting a 2-ethenyl-azoline of the formula with an approximately molar equivalent of 2- nitropropane. in the presence of 0À5-5À0% by wt. of azoline of a condensation catalyst by heating the mixture at reflux until the pot temperature is 150 C. The compounds are also made by heating 1 mol. of an azoline of the Formula (III) with 1 mol. of formaldehyde, or a compound yielding formaldehyde under the reaction conditions, to form the 2-ethenyl-azoline of the above formula, and subsequently adding 1 mol. of 2-nitropropane and 0À5-5À0% by wt. of azoline, of a condensation catalyst and a water entraining agent, and heating the resulting mixture to 150 C.; if desired, the nitroalkane can be added with the formaldehyde. A third method of preparation comprises heating a mixture of 1 mol. of an azoline of the above 1 mol. of 2-nitro-2-methyl- 1 -propanol and 0À5- 5À0% by wt. of azoline of a condensation catalyst to 100-200 C. while removing the water of reaction with a water-entraining agent. Preferred condensation catalysts are iodine, p-xylenesulphonic acid, zinc chloride and sodium hydrogen sulphate. Examples relate to the preparation of oxazolines and imidazolines. The novel compounds are used as plasticizers for nitrocellulose (see Division C3).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US488776A US3354171A (en) | 1965-09-20 | 1965-09-20 | Nitroazoline compounds and process therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1135093A true GB1135093A (en) | 1968-11-27 |
Family
ID=23941083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24642/66A Expired GB1135093A (en) | 1965-09-20 | 1966-06-02 | Nitroazoline compounds and their preparation |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3354171A (en) |
| BE (1) | BE685951A (en) |
| DE (1) | DE1670356B2 (en) |
| GB (1) | GB1135093A (en) |
Families Citing this family (2)
| 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 |
Family Cites Families (1)
| 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 |
-
1965
- 1965-09-20 US US488776A patent/US3354171A/en not_active Expired - Lifetime
-
1966
- 1966-06-02 GB GB24642/66A patent/GB1135093A/en not_active Expired
- 1966-06-28 DE DE1966C0039462 patent/DE1670356B2/en active Granted
- 1966-08-24 BE BE685951D patent/BE685951A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1670356A1 (en) | 1972-04-27 |
| BE685951A (en) | 1967-02-01 |
| US3354171A (en) | 1967-11-21 |
| DE1670356B2 (en) | 1976-08-19 |
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