PL81569B1 - Herbicidal alpha-naphthoxy-acetamides - from alpha-naphthoxyacetic acids via acid chlorides[DE2154435A1] - Google Patents
Herbicidal alpha-naphthoxy-acetamides - from alpha-naphthoxyacetic acids via acid chlorides[DE2154435A1] Download PDFInfo
- Publication number
- PL81569B1 PL81569B1 PL15144671A PL15144671A PL81569B1 PL 81569 B1 PL81569 B1 PL 81569B1 PL 15144671 A PL15144671 A PL 15144671A PL 15144671 A PL15144671 A PL 15144671A PL 81569 B1 PL81569 B1 PL 81569B1
- Authority
- PL
- Poland
- Prior art keywords
- alpha
- acid
- naphthoxy
- acetamides
- herbicidal
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 4
- 230000002363 herbicidal effect Effects 0.000 title description 2
- GHRYSOFWKRRLMI-UHFFFAOYSA-N 1-naphthyloxyacetic acid Chemical class C1=CC=C2C(OCC(=O)O)=CC=CC2=C1 GHRYSOFWKRRLMI-UHFFFAOYSA-N 0.000 title 1
- DEZGTCIAWFYNLJ-UHFFFAOYSA-N 2-naphthalen-1-yloxyacetamide Chemical class C1=CC=C2C(OCC(=O)N)=CC=CC2=C1 DEZGTCIAWFYNLJ-UHFFFAOYSA-N 0.000 title 1
- 150000001805 chlorine compounds Chemical class 0.000 title 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- HMIVVAPMRQMNAK-UHFFFAOYSA-N NOP Chemical compound C1=CC=CC2=CC(OC(C)C(O)=O)=CC=C21 HMIVVAPMRQMNAK-UHFFFAOYSA-N 0.000 claims description 8
- RURKHEGTHHTXJT-UHFFFAOYSA-N 2-naphthalen-1-yloxypropanoyl chloride Chemical compound C1=CC=C2C(OC(C)C(Cl)=O)=CC=CC2=C1 RURKHEGTHHTXJT-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 α-naphthoxy Chemical group 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VPSKMQYCSCPAGT-UHFFFAOYSA-N 2-bromo-n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)C(C)Br VPSKMQYCSCPAGT-UHFFFAOYSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- ZBOBHFDVBPNIDH-UHFFFAOYSA-N n'-methylethanimidamide;hydrochloride Chemical compound Cl.CNC(C)=N ZBOBHFDVBPNIDH-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8623070A | 1970-11-02 | 1970-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81569B1 true PL81569B1 (en) | 1975-08-30 |
Family
ID=22197142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15144671A PL81569B1 (en) | 1970-11-02 | 1971-11-02 | Herbicidal alpha-naphthoxy-acetamides - from alpha-naphthoxyacetic acids via acid chlorides[DE2154435A1] |
Country Status (4)
| Country | Link |
|---|---|
| BR (1) | BR7107358D0 (enExample) |
| DE (1) | DE2154435A1 (enExample) |
| HU (1) | HU164126B (enExample) |
| PL (1) | PL81569B1 (enExample) |
-
1971
- 1971-11-02 PL PL15144671A patent/PL81569B1/pl unknown
- 1971-11-02 DE DE19712154435 patent/DE2154435A1/de not_active Withdrawn
- 1971-11-02 HU HUSA002272 patent/HU164126B/hu unknown
- 1971-11-03 BR BR735871A patent/BR7107358D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2154435A1 (en) | 1972-05-10 |
| HU164126B (enExample) | 1973-12-28 |
| BR7107358D0 (pt) | 1973-05-08 |
| AU3521971A (en) | 1973-05-10 |
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