US3452080A - Vinylphosphinimines and a method of preparation - Google Patents
Vinylphosphinimines and a method of preparation Download PDFInfo
- Publication number
- US3452080A US3452080A US517474A US3452080DA US3452080A US 3452080 A US3452080 A US 3452080A US 517474 A US517474 A US 517474A US 3452080D A US3452080D A US 3452080DA US 3452080 A US3452080 A US 3452080A
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- carbon atoms
- phenyl
- alkyl
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- hydrogen
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- 238000000034 method Methods 0.000 title description 20
- 238000002360 preparation method Methods 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 125000000217 alkyl group Chemical group 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- -1 phenoxy, benzyl Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- UEQYFPCXXRUPKQ-UHFFFAOYSA-N azidoethene Chemical class C=CN=[N+]=[N-] UEQYFPCXXRUPKQ-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 102220029901 rs140332992 Human genes 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5355—Phosphoranes containing the structure P=N-
Definitions
- This invention relates to a novel process by which new and useful compounds can be formed.
- compounds with useful ph-ytotoxic properties can be produced. These compounds are useful in inhibiting the growth of noxious vegetation.
- R is selected from the class consisting of alkyl of up to twelve carbon atoms and phenyl; wherein R is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms, and phenyl; wherein R" is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms, phenyl and benzyl; and wherein R is selected from the class consisting of alkyl of up to twelve carbon atoms, alkoxy of up to twelve carbon atoms, amino, monoalkylamino having up to four carbon atoms in the alkyl moiety, dialkylamino having up to four carbon atoms in each alkyl moiety, the aromatic radicals of the class consisting of phenyl, phenoxy, benzyl, benzoxy and the said aromatic radicals containing substituents selected from the class consisting of alkyl of up to four carbon atoms, chlorine, bromine and nitro.
- This novel reaction is conducted in a chlorinated hydrocarbon solution and preferably in a solvent of lowboiling point, such as chloroform, methylene chloride, carbon tetrachloride or ethylene dichloride.
- a solvent of lowboiling point such as chloroform, methylene chloride, carbon tetrachloride or ethylene dichloride.
- Low to moderate temperatures about 20 C. to 40 C.
- the reaction evolves nitrogen and can be continued until the reaction is completed and the nitrogen evolution subsides.
- the desired products may be separated in crystalline form by diluting the reaction mixture with aliphatic h-ydrocarbons such as pentane, hexane and heptane. Sufficient of the aliphatic hydrocarbon should be added to induce turbidity.
- the mixture may be filtered after cooling and the precipitate further purified by recrystallization from a mixture of the described chlorinated hydrocarbons and the aliphatic hydrocarbons.
- Example 1 The procedure of Example 1 was repeated except that triphenylphosphine was reacted with ethyl fi-azido-amethylcrotonate. The resulting product was identified as ethyl 13- (triphenylphosphinimino -u-methylcrotonate.
- Example 3 The procedure of Example 1 was repeated using tri-nbutylphosphine in place of triphenylphosphine. The resulting product was ethyl ,B-(tri-n-butylphosphinimino) crotonate.
- Example 4 The reaction of triphenylphosphine and ,B-azido-crotonamide conducted in accordance with the general procedure of Example 1 resulted in a compound identified as 8-(triphenylphosphinimino)crotonamide.
- Example 5 N,N-diethyl 3-azido-2-methylcrotonamide was reacted with triphenylphosphine by disolving the reactant in chloroform at 35 C.
- the product separated from the reaction mixture was identified as N,N-diethyl-,B-(triphenylphosphinimino -u-methylcrotonamide.
- Example 6 Ethyl ,G-azido-phenyl was reacted with triphenylphosphine by the procedure of Example 1 whereby a product was produced having the formula Example 7
- the reaction of tri(n-butyl)phosphine with nitrophenyl B-azidocrotonate by the general procedure of Example 1 resulted in the formation of p-nitrophenyl fi-(tri-n-butylphosphinimino) crotonate.
- Example 8 a-Phenyl-B-azidocrotonamide was reacted with triphenylphosphine by the procedure of Example 1.
- the product separated from the reaction mixture was identified as 8- (triphenylphosphinimino)-a-phenylcrotonamide.
- Example 9 The reaction of 4-chloropheny1 B-azidocrotonate with triphenylphosphine in accordance with the procedure of Example 1 produced p-chlorophenyl B-(triphenylphosphinimino) crotonate.
- Example 10 Triethylphosphine was reacted by the procedure of Example 1 with p-chlorobenzyl fi-azidocrotonate to pro prise p-chlorophenyl p (triethylphosphinimino)crotonate.
- Example 11 Triphenylphosphine was reacted with p-ethylphenyl fl-azidocrotonate by the procedure of Example 1 to produce p-ethylphenyl 13 (triphenylphosphinimino)crotonate.
- Example 12 By the procedure of Example 1 tri-n-butylphosphine was reacted with 3,4-d-ibromophenyl fl-azidocrotonate whereby 3,4- dibromophenyl B (tri-n-butylphosphinimino) crotonate was formed.
- Example 13 Using the procedure of Example 1 and reacting triphenylphosphine with fi-azido oa-phenylcrotonamide, a compound identified as B-triphenylphosphinimino a-phenylcrotonamide was produced.
- Example 14 By the procedure of Example 1, ,B-azido Z-methylvinyl benzyl ketone was reacted with triphenylphosphine. A compound of the following formula was produced:
- R is phenyl, R and R" are hydrogen, and R is ethoxy.
- R is phenyl, R' and R" are each hydrogen, and R is amino.
- R is phenyl, R is hydrogen, R" is methyl and R' is amino.
- R is phenyl, R and R are each hydrogen, and R is amino.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,452,080 VINYLPHOSPHINIMINES AND A METHOD OF PREPARATION George R. Harvey, Kirkwood, and Kenneth Wayne Ratts, Creve Coeur, Mo., assignors to Monsanto Company,
St. Louis, Mo., a corporation of Delaware No Drawing. Filed Dec. 29, 1965, Ser. No. 517,474 Int. Cl. C07f 9/02 U.S. Cl. 260-471 9 Claims ABSTRACT OF THE DISCLOSURE Vinylphosphinimines of the formula RI C lHz R O R,P=N t'-l 1t wherein R is selected from the group consisting of alkyl having up to 12 carbon atoms and phenyl; R is selected from the group consisting of hydrogen, alkyl having up to 4 carbon atoms and phenyl; R" is selected from the group consisting of hydrogen, alkyl having up to 4 carbon atoms, phenyl and benzyl; and R is selected from the group Consisting of alkyl having up to 12 carbon atoms, alkoxy having up to 12 carbon atoms, amino, monoand dialkylamino having up to four carbon atoms in each alkyl moiety, aromatic radicals selected from the group consisting of phenyl, phenoxy, benzyl, benzoxy and said aromatic radicals containing substituents selected from the class consisting of alkyl having up to four carbon atoms, chlorine, bromine and nitro; prepared by the reaction in a chlorinated hydrocarbon of the appropriate fl-azido compound with the appropriate phosphine.
These compounds have phytotoxic properties.
This invention relates to a novel process by which new and useful compounds can be formed. By the reaction of a class of vinyl azides with phosphines, compounds with useful ph-ytotoxic properties can be produced. These compounds are useful in inhibiting the growth of noxious vegetation.
The vinyl azides useful in practicing this invention are described and claimed in copending application Ser. No. 517,488, filed Dec. 29, 1965, by George R. Harvey.
The novel reaction takes place in accordance with the equation:
wherein R is selected from the class consisting of alkyl of up to twelve carbon atoms and phenyl; wherein R is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms, and phenyl; wherein R" is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms, phenyl and benzyl; and wherein R is selected from the class consisting of alkyl of up to twelve carbon atoms, alkoxy of up to twelve carbon atoms, amino, monoalkylamino having up to four carbon atoms in the alkyl moiety, dialkylamino having up to four carbon atoms in each alkyl moiety, the aromatic radicals of the class consisting of phenyl, phenoxy, benzyl, benzoxy and the said aromatic radicals containing substituents selected from the class consisting of alkyl of up to four carbon atoms, chlorine, bromine and nitro.
This novel reaction is conducted in a chlorinated hydrocarbon solution and preferably in a solvent of lowboiling point, such as chloroform, methylene chloride, carbon tetrachloride or ethylene dichloride. Low to moderate temperatures (about 20 C. to 40 C.) may be used so as to avoid a too vigorous reaction. The reaction evolves nitrogen and can be continued until the reaction is completed and the nitrogen evolution subsides.
The desired products may be separated in crystalline form by diluting the reaction mixture with aliphatic h-ydrocarbons such as pentane, hexane and heptane. Sufficient of the aliphatic hydrocarbon should be added to induce turbidity. The mixture may be filtered after cooling and the precipitate further purified by recrystallization from a mixture of the described chlorinated hydrocarbons and the aliphatic hydrocarbons.
Further details of the preparation of the new com pounds are set forth in the following examples.
Example 1 Example 2 The procedure of Example 1 was repeated except that triphenylphosphine was reacted with ethyl fi-azido-amethylcrotonate. The resulting product was identified as ethyl 13- (triphenylphosphinimino -u-methylcrotonate.
Example 3 The procedure of Example 1 was repeated using tri-nbutylphosphine in place of triphenylphosphine. The resulting product was ethyl ,B-(tri-n-butylphosphinimino) crotonate.
Example 4 The reaction of triphenylphosphine and ,B-azido-crotonamide conducted in accordance with the general procedure of Example 1 resulted in a compound identified as 8-(triphenylphosphinimino)crotonamide.
Example 5 N,N-diethyl 3-azido-2-methylcrotonamide was reacted with triphenylphosphine by disolving the reactant in chloroform at 35 C. The product separated from the reaction mixture was identified as N,N-diethyl-,B-(triphenylphosphinimino -u-methylcrotonamide.
Example 6 Ethyl ,G-azido-phenyl was reacted with triphenylphosphine by the procedure of Example 1 whereby a product was produced having the formula Example 7 The reaction of tri(n-butyl)phosphine with nitrophenyl B-azidocrotonate by the general procedure of Example 1 resulted in the formation of p-nitrophenyl fi-(tri-n-butylphosphinimino) crotonate.
Example 8 a-Phenyl-B-azidocrotonamide was reacted with triphenylphosphine by the procedure of Example 1. The product separated from the reaction mixture was identified as 8- (triphenylphosphinimino)-a-phenylcrotonamide.
Example 9 The reaction of 4-chloropheny1 B-azidocrotonate with triphenylphosphine in accordance with the procedure of Example 1 produced p-chlorophenyl B-(triphenylphosphinimino) crotonate.
Example 10 Triethylphosphine was reacted by the procedure of Example 1 with p-chlorobenzyl fi-azidocrotonate to pro duce p-chlorophenyl p (triethylphosphinimino)crotonate.
Example 11 Triphenylphosphine was reacted with p-ethylphenyl fl-azidocrotonate by the procedure of Example 1 to produce p-ethylphenyl 13 (triphenylphosphinimino)crotonate.
Example 12 By the procedure of Example 1 tri-n-butylphosphine was reacted with 3,4-d-ibromophenyl fl-azidocrotonate whereby 3,4- dibromophenyl B (tri-n-butylphosphinimino) crotonate was formed.
Example 13 Using the procedure of Example 1 and reacting triphenylphosphine with fi-azido oa-phenylcrotonamide, a compound identified as B-triphenylphosphinimino a-phenylcrotonamide was produced.
Example 14 By the procedure of Example 1, ,B-azido Z-methylvinyl benzyl ketone was reacted with triphenylphosphine. A compound of the following formula was produced:
0 P=N-( 3=GHz( iCHi Following the procedure of Example 1, triethylphos- RI Bib R" (H) R31==No=( J-c-R'" wherein R is selected from the class consisting of alkyl having up to twelve carbon atoms and phenyl; wherein R is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms and phenyl; wherein R" is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms, phenyl and benzyl; and wherein R'" is selected from the class consisting of alkyl of up to twelve carbon atoms, alkoxy of up to twelve carbon atoms, amino, monoalkylamino having up to four carbon atoms in the alkyl moiety, dialkylamino having up to four carbon atoms in each alkyl moiety, the aromatic radicals selected from the class consisting of benzyl, benzoxy, phenyl, phenoxy and the said aromatic radicals containing substituents selected from the class consisting of alkyl of up to four carbon atoms, chlorine, bromine and nitro.
2. A compound defined by claim 1 wherein R is phenyl, R and R" are hydrogen, and R is ethoxy.
3. A compound defined by claim 1 wherein R is phenyl, R is hydrogen, R" is methyl and R' is ethoxy.
4. A compound defined by claim 1 wherein R is phenyl, R' and R" are each hydrogen, and R is amino.
5. A compound defined by claim 1 wherein R is phenyl, R is hydrogen, R" is methyl and R' is amino.
6. A method of preparing a compound of the formula wherein R is selected from the class consisting of alkyl having up to twelve carbon atoms and phenyl; wherein R is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms and phenyl; wherein R is selected from the class consisting of hydrogen, alkyl of up to four carbon atoms, phenyl and benzyl; and wherein R' is selected from the class consisting of alkyl of up to twelve carbon atoms, alkoxy of up to twelve carbon atoms, amino, monoalkylamino having up to four carbon atoms in the alkyl moiety, dialkylamino having up to four carbon atoms in each alkyl moiety, the aromatic radicals selected from the class consisting of benzyl, benzoxy, phenyl, phenoxy and the said aromatic radicals containing substituents selected from the class consisting of alkyl of up to four carbon atoms, chlorine, bromine and nitro; which comprises reacting in a chlorinated hydrocarbon solvent a compound of the formula 7. A method defined by claim 6 wherein R is phenyl, R and R" are each hydrogen, and R'" is ethoxy.
8. A method defined by claim 6 wherein R is phenyl, R is hydrogen, R" is methyl, and R is ethoxy.
9. A method defined by claim 6 wherein R is phenyl, R and R are each hydrogen, and R is amino.
References Cited Journal of Organic Chemistry, by Leifier et al., vol. 28 (April 1963), QD24156, pp. 902-906 relied on.
LORRAINE A. WEINBERGER, Primary Examiner.
L. A. 'I'HAXTON, Assistant Examiner.
US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51747465A | 1965-12-29 | 1965-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3452080A true US3452080A (en) | 1969-06-24 |
Family
ID=24059957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US517474A Expired - Lifetime US3452080A (en) | 1965-12-29 | 1965-12-29 | Vinylphosphinimines and a method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3452080A (en) |
-
1965
- 1965-12-29 US US517474A patent/US3452080A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
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