DE2403708C3 - Verfahren zur Herstellung von 2-Methyl-5,6-dihydropyran-3-carbonsäureanilid - Google Patents
Verfahren zur Herstellung von 2-Methyl-5,6-dihydropyran-3-carbonsäureanilidInfo
- Publication number
- DE2403708C3 DE2403708C3 DE2403708A DE2403708A DE2403708C3 DE 2403708 C3 DE2403708 C3 DE 2403708C3 DE 2403708 A DE2403708 A DE 2403708A DE 2403708 A DE2403708 A DE 2403708A DE 2403708 C3 DE2403708 C3 DE 2403708C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- carboxylic acid
- dihydropyran
- aniline
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 14
- NPTRDZWZSUYBAG-UHFFFAOYSA-N 6-methyl-n-phenyl-3,6-dihydro-2h-pyran-5-carboxamide Chemical compound CC1OCCC=C1C(=O)NC1=CC=CC=C1 NPTRDZWZSUYBAG-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 26
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QSYWYGWXCVQLAP-UHFFFAOYSA-N 6-methyl-3,6-dihydro-2h-pyran-5-carboxylic acid Chemical compound CC1OCCC=C1C(O)=O QSYWYGWXCVQLAP-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WRBCQUGCVQQKHY-UHFFFAOYSA-N methyl 6-methyl-3,6-dihydro-2H-pyran-5-carboxylate Chemical compound COC(=O)C=1C(OCCC1)C WRBCQUGCVQQKHY-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YFTILIIWZJSSOK-UHFFFAOYSA-N 6-methyl-3,6-dihydro-2h-pyran-5-carbonyl chloride Chemical compound CC1OCCC=C1C(Cl)=O YFTILIIWZJSSOK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- -1 inorganic acid chlorides Chemical class 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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 description 1
- UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 description 1
- KADNPUPOAGYBLQ-UHFFFAOYSA-N 6-methyl-2,3-dihydropyran-6-carboxylic acid Chemical compound CC1(OCCC=C1)C(=O)O KADNPUPOAGYBLQ-UHFFFAOYSA-N 0.000 description 1
- 229930186657 Lat Natural products 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- LUOYACCQSOFAAA-UHFFFAOYSA-N ethyl 6-methyl-3,6-dihydro-2h-pyran-5-carboxylate Chemical compound CCOC(=O)C1=CCCOC1C LUOYACCQSOFAAA-UHFFFAOYSA-N 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2403708A DE2403708C3 (de) | 1974-01-26 | 1974-01-26 | Verfahren zur Herstellung von 2-Methyl-5,6-dihydropyran-3-carbonsäureanilid |
| ZA00750311A ZA75311B (en) | 1974-01-26 | 1975-01-16 | Process for the manufacture of 2-methyl-5,6-dihydropyran-3-carboxylic acid anilide |
| NL7500688A NL7500688A (nl) | 1974-01-26 | 1975-01-21 | Werkwijze voor het bereiden van 2-methyl-5,6-di- hydropyran-3-carbonzuuranlide. |
| IL46466A IL46466A0 (en) | 1974-01-26 | 1975-01-21 | Process for the manufacture of 2-methyl-5,6-dihydropyran-3-carboxylic acid anilide |
| CS7500000446A CS181169B2 (en) | 1974-01-26 | 1975-01-22 | Method of preparing anilide of 2-methyl-5,6-dihydropyrane-3-carboxylic acid |
| CH79675A CH595373A5 (en, 2012) | 1974-01-26 | 1975-01-23 | |
| HU75HO1765A HU170706B (en, 2012) | 1974-01-26 | 1975-01-23 | |
| AR257411A AR209291A1 (es) | 1974-01-26 | 1975-01-24 | Procedimiento para la obtencion de 2-metil-5,6-dihidropiran-3-carboxilanilida |
| AT56275A AT339299B (de) | 1974-01-26 | 1975-01-24 | Verfahren zur herstellung von 2-methyl-5,6-dihydropyran-3-carbonsaureanilid |
| DD183806A DD115902A5 (en, 2012) | 1974-01-26 | 1975-01-24 | |
| IT19579/75A IT1031145B (it) | 1974-01-26 | 1975-01-24 | Processo per la preparazione della anilde dell acido 2 me til |
| GB325475A GB1472967A (en) | 1974-01-26 | 1975-01-24 | Process for the manufacture of 2-methyl-5,6-dihydropyran- |
| JP50009907A JPS50106966A (en, 2012) | 1974-01-26 | 1975-01-24 | |
| AU77604/75A AU7760475A (en) | 1974-01-26 | 1975-01-24 | Manufacture of 2-methyl-5,6-dihydropyran-3-carboxylic acid anilide |
| SU2099682A SU528034A3 (ru) | 1974-01-26 | 1975-01-24 | Способ получени анилида 2-метил-5,6-дигидропиран-3-карбоновой кислоты |
| SE7500763A SE396077B (sv) | 1974-01-26 | 1975-01-24 | Forfarande for framstellning av 2-metyl-5,6-dihydropyran-3-karbonsyraanilid |
| BR506/75A BR7500506A (pt) | 1974-01-26 | 1975-01-24 | Processo para a preparacao de anilida de acido 2-metil-5 6-dihidro-pirano-3-carboxilico |
| RO7581234A RO71303A (ro) | 1974-01-26 | 1975-01-24 | Procedeu pentru prepararea anilidei acidului 2-metil-5,6-dihidropiran-3-carboxilic |
| FR7502389A FR2259100B1 (en, 2012) | 1974-01-26 | 1975-01-27 | |
| BE152734A BE824814A (fr) | 1974-01-26 | 1975-01-27 | Procede de preparation de l'anilide de l'acide methyl-2 dihydro-5,6 pyranne-carboxylique-3 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2403708A DE2403708C3 (de) | 1974-01-26 | 1974-01-26 | Verfahren zur Herstellung von 2-Methyl-5,6-dihydropyran-3-carbonsäureanilid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2403708A1 DE2403708A1 (de) | 1975-08-14 |
| DE2403708B2 DE2403708B2 (de) | 1979-03-15 |
| DE2403708C3 true DE2403708C3 (de) | 1979-11-15 |
Family
ID=5905738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2403708A Expired DE2403708C3 (de) | 1974-01-26 | 1974-01-26 | Verfahren zur Herstellung von 2-Methyl-5,6-dihydropyran-3-carbonsäureanilid |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS50106966A (en, 2012) |
| AR (1) | AR209291A1 (en, 2012) |
| AT (1) | AT339299B (en, 2012) |
| AU (1) | AU7760475A (en, 2012) |
| BE (1) | BE824814A (en, 2012) |
| BR (1) | BR7500506A (en, 2012) |
| CH (1) | CH595373A5 (en, 2012) |
| CS (1) | CS181169B2 (en, 2012) |
| DD (1) | DD115902A5 (en, 2012) |
| DE (1) | DE2403708C3 (en, 2012) |
| FR (1) | FR2259100B1 (en, 2012) |
| GB (1) | GB1472967A (en, 2012) |
| HU (1) | HU170706B (en, 2012) |
| IL (1) | IL46466A0 (en, 2012) |
| IT (1) | IT1031145B (en, 2012) |
| NL (1) | NL7500688A (en, 2012) |
| RO (1) | RO71303A (en, 2012) |
| SE (1) | SE396077B (en, 2012) |
| SU (1) | SU528034A3 (en, 2012) |
| ZA (1) | ZA75311B (en, 2012) |
-
1974
- 1974-01-26 DE DE2403708A patent/DE2403708C3/de not_active Expired
-
1975
- 1975-01-16 ZA ZA00750311A patent/ZA75311B/xx unknown
- 1975-01-21 IL IL46466A patent/IL46466A0/xx unknown
- 1975-01-21 NL NL7500688A patent/NL7500688A/xx not_active Application Discontinuation
- 1975-01-22 CS CS7500000446A patent/CS181169B2/cs unknown
- 1975-01-23 HU HU75HO1765A patent/HU170706B/hu unknown
- 1975-01-23 CH CH79675A patent/CH595373A5/xx not_active IP Right Cessation
- 1975-01-24 RO RO7581234A patent/RO71303A/ro unknown
- 1975-01-24 SE SE7500763A patent/SE396077B/xx unknown
- 1975-01-24 JP JP50009907A patent/JPS50106966A/ja active Pending
- 1975-01-24 AR AR257411A patent/AR209291A1/es active
- 1975-01-24 AU AU77604/75A patent/AU7760475A/en not_active Expired
- 1975-01-24 IT IT19579/75A patent/IT1031145B/it active
- 1975-01-24 GB GB325475A patent/GB1472967A/en not_active Expired
- 1975-01-24 SU SU2099682A patent/SU528034A3/ru active
- 1975-01-24 BR BR506/75A patent/BR7500506A/pt unknown
- 1975-01-24 DD DD183806A patent/DD115902A5/xx unknown
- 1975-01-24 AT AT56275A patent/AT339299B/de not_active IP Right Cessation
- 1975-01-27 BE BE152734A patent/BE824814A/xx not_active IP Right Cessation
- 1975-01-27 FR FR7502389A patent/FR2259100B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR209291A1 (es) | 1977-04-15 |
| DE2403708A1 (de) | 1975-08-14 |
| IT1031145B (it) | 1979-04-30 |
| NL7500688A (nl) | 1975-07-29 |
| JPS50106966A (en, 2012) | 1975-08-22 |
| FR2259100B1 (en, 2012) | 1978-02-24 |
| HU170706B (en, 2012) | 1977-08-28 |
| SE396077B (sv) | 1977-09-05 |
| CS181169B2 (en) | 1978-03-31 |
| ZA75311B (en) | 1976-01-28 |
| IL46466A0 (en) | 1975-04-25 |
| SU528034A3 (ru) | 1976-09-05 |
| SE7500763L (en, 2012) | 1975-07-28 |
| DD115902A5 (en, 2012) | 1975-10-20 |
| RO71303A (ro) | 1982-12-06 |
| CH595373A5 (en, 2012) | 1978-02-15 |
| AU7760475A (en) | 1976-07-29 |
| BR7500506A (pt) | 1975-11-11 |
| DE2403708B2 (de) | 1979-03-15 |
| ATA56275A (de) | 1977-02-15 |
| BE824814A (fr) | 1975-07-28 |
| FR2259100A1 (en, 2012) | 1975-08-22 |
| AT339299B (de) | 1977-10-10 |
| GB1472967A (en) | 1977-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BI | Miscellaneous see part 2 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |