CH550806A - Verfahren zur herstellung von o-substituierten oxymethylpyrimidinen. - Google Patents
Verfahren zur herstellung von o-substituierten oxymethylpyrimidinen.Info
- Publication number
- CH550806A CH550806A CH725171A CH725171A CH550806A CH 550806 A CH550806 A CH 550806A CH 725171 A CH725171 A CH 725171A CH 725171 A CH725171 A CH 725171A CH 550806 A CH550806 A CH 550806A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- iii
- aryl
- formula
- alkali metal
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 title claims abstract description 7
- 229940031826 phenolate Drugs 0.000 title claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 title abstract 3
- 150000001340 alkali metals Chemical class 0.000 title abstract 2
- AROGQTWAAJTEFR-UHFFFAOYSA-N 4-(chloromethyl)pyrimidine Chemical compound ClCC1=CC=NC=N1 AROGQTWAAJTEFR-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- MSFVEEFXECBJPG-UHFFFAOYSA-N 2-(chloromethyl)pyrimidine Chemical class ClCC1=NC=CC=N1 MSFVEEFXECBJPG-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 19
- -1 amidine hydrochloride Chemical class 0.000 abstract description 6
- 239000000417 fungicide Substances 0.000 abstract description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 230000001069 nematicidal effect Effects 0.000 abstract description 2
- 239000005645 nematicide Substances 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 8
- ZKCAVUYFKJKMRI-UHFFFAOYSA-N 6-(chloromethyl)-2-propan-2-yl-1h-pyrimidin-4-one Chemical compound CC(C)C1=NC(=O)C=C(CCl)N1 ZKCAVUYFKJKMRI-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- AKSJYXATJHTXMO-UHFFFAOYSA-N 6-(methoxymethyl)-2-propan-2-yl-1h-pyrimidin-4-one Chemical compound COCC1=CC(=O)N=C(C(C)C)N1 AKSJYXATJHTXMO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UWVBMQJUKLGENY-UHFFFAOYSA-N 4-(octoxymethyl)-2-propan-2-yl-1H-pyrimidin-6-one Chemical compound OC1=NC(=NC(=C1)COCCCCCCCC)C(C)C UWVBMQJUKLGENY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VWXLCWNPSOUPPE-UHFFFAOYSA-N (1-amino-2-methylpropylidene)azanium;chloride Chemical compound Cl.CC(C)C(N)=N VWXLCWNPSOUPPE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DKOIHIKBGZYRTN-UHFFFAOYSA-N 4-(methoxymethyl)-6-methylpyrimidin-2-amine Chemical compound COCC1=CC(C)=NC(N)=N1 DKOIHIKBGZYRTN-UHFFFAOYSA-N 0.000 description 1
- ADHMBPXGHYLKPQ-UHFFFAOYSA-N 5-methoxy-6-(methoxymethyl)-1h-pyrimidin-4-one Chemical compound COCC1=NC=NC(O)=C1OC ADHMBPXGHYLKPQ-UHFFFAOYSA-N 0.000 description 1
- DTHAPSZAKFKWHB-UHFFFAOYSA-N 6-(ethoxymethyl)-2-methyl-1h-pyrimidin-4-one Chemical compound CCOCC1=CC(=O)N=C(C)N1 DTHAPSZAKFKWHB-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KNFXXAGQEUUZAZ-UHFFFAOYSA-N ethyl ethaneperoxoate Chemical compound CCOOC(C)=O KNFXXAGQEUUZAZ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH725171A CH550806A (de) | 1971-05-18 | 1971-05-18 | Verfahren zur herstellung von o-substituierten oxymethylpyrimidinen. |
| NL7204238A NL7204238A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-18 | 1972-03-29 | |
| DD16296672A DD97888A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-18 | 1972-05-15 | |
| GB1417472A GB1337897A (en) | 1971-05-18 | 1972-05-15 | Process for the preparation of o-substituted hydroxy-methyl- pyrimidines |
| DE19722223856 DE2223856A1 (de) | 1971-05-18 | 1972-05-16 | Verfahren zur Herstellung von neuen o-substituiertenOxymethylpyrimidinen |
| LU65368D LU65368A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-18 | 1972-05-16 | |
| CS334972A CS178109B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-18 | 1972-05-17 | |
| IT5029372A IT965787B (it) | 1971-05-18 | 1972-05-17 | Procedimento per produrre ossi metil pirimidine sostituite in posizione orto |
| BE783637A BE783637A (fr) | 1971-05-18 | 1972-05-17 | Oxymethylpyrimidines ortho-substituees et leurs procedes de preparatio |
| AT434772A AT316562B (de) | 1971-05-18 | 1972-05-18 | Verfahren zur Herstellung von o-substituierten Oxymethylpyrimidinen |
| FR7217937A FR2138131B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-05-18 | 1972-05-18 | |
| IT2812172A IT965737B (it) | 1971-05-18 | 1972-08-11 | Veicolo con dispositivo di carica mento specie per casse iprocedimento per produrre ossi metil pirimidine sostituiten calce struzzo in posizione orto |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH725171A CH550806A (de) | 1971-05-18 | 1971-05-18 | Verfahren zur herstellung von o-substituierten oxymethylpyrimidinen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH550806A true CH550806A (de) | 1974-06-28 |
Family
ID=4322204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH725171A CH550806A (de) | 1971-05-18 | 1971-05-18 | Verfahren zur herstellung von o-substituierten oxymethylpyrimidinen. |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH550806A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| CS (1) | CS178109B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1971
- 1971-05-18 CH CH725171A patent/CH550806A/de not_active IP Right Cessation
-
1972
- 1972-05-17 CS CS334972A patent/CS178109B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS178109B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |