CA2118460A1 - Procede de production de pyrimidylphosphates dialkyliques - Google Patents

Procede de production de pyrimidylphosphates dialkyliques

Info

Publication number: CA2118460A1
Authority: CA; Canada
Prior art keywords: dialkyl; hydroxypyrimidine; organic; organic solvent; alkali metal
Prior art date: 1993-11-12
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.): Abandoned

Application number

CA 2118460

Other languages

English (en)

Inventor

Daniel M. Wasleski

David T. Erdman

Peter E. Newallis

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Corp

Original Assignee

Miles Inc

Priority date (The priority date 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 date listed.)

1993-11-12

Filing date

1994-10-19

Publication date

1995-05-13

1994-10-19 Application filed by Miles Inc filed Critical Miles Inc

1995-05-13 Publication of CA2118460A1 publication Critical patent/CA2118460A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 39
238000004519 manufacturing process Methods 0.000 title claims abstract description 9
LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 claims abstract description 19
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 13
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 11
239000003960 organic solvent Substances 0.000 claims abstract description 9
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
239000008346 aqueous phase Substances 0.000 claims description 6
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 6
JARZKOYAUVCWCZ-UHFFFAOYSA-N 2-tert-butylpyrimidin-5-ol Chemical group CC(C)(C)C1=NC=C(O)C=N1 JARZKOYAUVCWCZ-UHFFFAOYSA-N 0.000 claims description 5
239000003849 aromatic solvent Substances 0.000 claims description 5
239000010410 layer Substances 0.000 claims description 5
239000012074 organic phase Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
238000013019 agitation Methods 0.000 claims description 3
VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 claims description 3
239000012044 organic layer Substances 0.000 claims description 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
CHLCGLVMIQCUNA-UHFFFAOYSA-N CCOC(C)(C)OP(O)(Cl)=S Chemical group CCOC(C)(C)OP(O)(Cl)=S CHLCGLVMIQCUNA-UHFFFAOYSA-N 0.000 claims 1
UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
239000000575 pesticide Substances 0.000 abstract description 2
239000002917 insecticide Substances 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 description 7
239000000203 mixture Substances 0.000 description 7
-1 alkali metal phenoxide Chemical class 0.000 description 5
HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
OQZGLXOADHKTDN-UHFFFAOYSA-N 1-oxidopyrimidin-1-ium Chemical compound [O-][N+]1=CC=CN=C1 OQZGLXOADHKTDN-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
QTIJUIDBXKIGLG-UHFFFAOYSA-N 2-ethylpyrimidin-5-ol Chemical compound CCC1=NC=C(O)C=N1 QTIJUIDBXKIGLG-UHFFFAOYSA-N 0.000 description 1
XCEXBOISODMPOG-UHFFFAOYSA-N 2-propan-2-ylpyrimidin-5-ol Chemical compound CC(C)C1=NC=C(O)C=N1 XCEXBOISODMPOG-UHFFFAOYSA-N 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
241001414720 Cicadellidae Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
JHPRCMIXLDFYTE-UHFFFAOYSA-N chloro-hydroxy-propan-2-yloxy-sulfanylidene-lambda5-phosphane Chemical compound CC(C)OP(O)(Cl)=S JHPRCMIXLDFYTE-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 0.000 description 1

CA 2118460 1993-11-12 1994-10-19 Procede de production de pyrimidylphosphates dialkyliques Abandoned CA2118460A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US15132993A	1993-11-12	1993-11-12
US08/151,329		1993-11-12

Publications (1)

Publication Number	Publication Date
CA2118460A1 true CA2118460A1 (fr)	1995-05-13

Family

ID=22538266

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2118460 Abandoned CA2118460A1 (fr)	1993-11-12	1994-10-19	Procede de production de pyrimidylphosphates dialkyliques

Country Status (1)

Country	Link
CA (1)	CA2118460A1 (fr)

1994
- 1994-10-19 CA CA 2118460 patent/CA2118460A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
2001-10-03	EEER	Examination request
2004-10-19	FZDE	Dead

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US4130607A (en)	1978-12-19	Preparation of dithiophosphoric acid diester halides
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US4305891A (en)	1981-12-15	Method for preparing O-4-(hydroxyalkyl)-thiophenyl phosphates
US3862273A (en)	1975-01-21	Preparation of 0-aryl 0,0-dialkyl phosphorothioates
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US4229383A (en)	1980-10-21	Process for the preparation of phosphoramidates
US4391760A (en)	1983-07-05	S-(Tertiary alkyl) alkylphosphonothioic halides
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US3442928A (en)	1969-05-06	Preparation of n-(beta-dialkyldithiophosphorylethyl)alkyl carbamates and thiocarbamates
US3175003A (en)	1965-03-23	O, o'-(halomethyl) phosphinylidene oximes
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