CS208681B2 - Method of making the 5-kyan-4-methyl-1,3-oxazole - Google Patents
Method of making the 5-kyan-4-methyl-1,3-oxazole Download PDFInfo
- Publication number
- CS208681B2 CS208681B2 CS797376A CS737679A CS208681B2 CS 208681 B2 CS208681 B2 CS 208681B2 CS 797376 A CS797376 A CS 797376A CS 737679 A CS737679 A CS 737679A CS 208681 B2 CS208681 B2 CS 208681B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxazole
- methyl
- reaction
- catalyst
- anhydride
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 claims 1
- HBKBZJZRIWAICY-UHFFFAOYSA-N 4-methyl-1,3-oxazole-5-carboxamide Chemical compound CC=1N=COC=1C(N)=O HBKBZJZRIWAICY-UHFFFAOYSA-N 0.000 description 12
- JZSLPQXOLZCAME-UHFFFAOYSA-N 4-methyl-1,3-oxazole-5-carbonitrile Chemical compound CC=1N=COC=1C#N JZSLPQXOLZCAME-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 4
- 229940078494 nickel acetate Drugs 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- -1 carbonates Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229940076286 cupric acetate Drugs 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 208000013840 Non-involuting congenital hemangioma Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- UJJAMBDUJUGPRL-UHFFFAOYSA-N n-acetyl-4-methyl-1,3-oxazole-5-carboxamide Chemical compound CC(=O)NC(=O)C=1OC=NC=1C UJJAMBDUJUGPRL-UHFFFAOYSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782847625 DE2847625A1 (de) | 1978-11-02 | 1978-11-02 | Verfahren zur herstellung eines oxazols |
| CH730979 | 1979-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208681B2 true CS208681B2 (en) | 1981-09-15 |
Family
ID=25701104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS797376A CS208681B2 (en) | 1978-11-02 | 1979-10-30 | Method of making the 5-kyan-4-methyl-1,3-oxazole |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4255584A (pl) |
| EP (1) | EP0010697B1 (pl) |
| CA (1) | CA1122220A (pl) |
| CS (1) | CS208681B2 (pl) |
| DE (1) | DE2965390D1 (pl) |
| DK (1) | DK463779A (pl) |
| HU (1) | HU178014B (pl) |
| IE (1) | IE49102B1 (pl) |
| IL (1) | IL58568A (pl) |
| PL (1) | PL119233B1 (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0224706A1 (de) * | 1985-11-01 | 1987-06-10 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung eines Oxazols |
| US5214162A (en) * | 1990-12-21 | 1993-05-25 | Hoffman-La Roche Inc. | Process for manufacturing 5-cyano-4-lower alkyloxazoles |
| EP0612736B1 (de) * | 1993-02-25 | 1999-04-14 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von Oxazolderivaten |
| EP0770604A1 (de) * | 1995-10-25 | 1997-05-02 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von Oxazolderivaten |
| DE19604926A1 (de) * | 1996-02-10 | 1997-08-14 | Natec Reich Summer Gmbh Co Kg | Scheibenstapler, insbesondere für Käsescheiben |
| US5910594A (en) * | 1997-02-13 | 1999-06-08 | Roche Vitamins Inc. | Process for the manufacture of 5-cyano-4-lower alkyl-oxazoles |
| DE19801878A1 (de) | 1998-01-20 | 1999-08-19 | Natec | Verfahren und Vorrichtung zum Stapeln von unverpackten Schmelzkäsescheiben |
| EP2844634B1 (en) | 2012-05-03 | 2021-04-14 | DSM IP Assets B.V. | Process for the preparation of intermediate compounds for preparing vitamin b6 |
| CN104203929B (zh) | 2012-05-03 | 2017-11-17 | 帝斯曼知识产权资产管理有限公司 | 制备4‑甲基噁唑‑5‑羧酸酯的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB532938A (en) * | 1939-06-02 | 1941-02-04 | Rhone Poulenc Sa | Process for the manufacture of adipic nitrile |
| CH449623A (de) * | 1963-05-22 | 1968-01-15 | Hoffmann La Roche | Verfahren zur Herstellung von 4-Alkyl-5-cyan-oxazolen |
| NL6505181A (pl) * | 1965-04-23 | 1966-10-24 | ||
| US4026901A (en) * | 1975-04-30 | 1977-05-31 | Hoffmann-La Roche Inc. | Conversion of 4-lower alkyloxazole-5-carboxamide to 4-lower alkyl-5-cyanooxazoles |
| CH616415A5 (pl) * | 1975-07-11 | 1980-03-31 | Hoffmann La Roche |
-
1979
- 1979-10-16 CA CA000337708A patent/CA1122220A/en not_active Expired
- 1979-10-18 DE DE7979104030T patent/DE2965390D1/de not_active Expired
- 1979-10-18 EP EP79104030A patent/EP0010697B1/de not_active Expired
- 1979-10-26 IL IL58568A patent/IL58568A/xx unknown
- 1979-10-26 HU HU79HO2192A patent/HU178014B/hu unknown
- 1979-10-30 CS CS797376A patent/CS208681B2/cs unknown
- 1979-10-30 US US06/089,757 patent/US4255584A/en not_active Expired - Lifetime
- 1979-11-01 IE IE2096/79A patent/IE49102B1/en unknown
- 1979-11-01 DK DK463779A patent/DK463779A/da not_active Application Discontinuation
- 1979-11-02 PL PL1979219403A patent/PL119233B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0010697B1 (de) | 1983-05-11 |
| IL58568A (en) | 1983-10-31 |
| US4255584A (en) | 1981-03-10 |
| DK463779A (da) | 1980-05-03 |
| PL219403A1 (pl) | 1980-08-11 |
| DE2965390D1 (en) | 1983-06-16 |
| IL58568A0 (en) | 1980-01-31 |
| HU178014B (en) | 1982-02-28 |
| PL119233B1 (en) | 1981-12-31 |
| IE792096L (en) | 1980-05-02 |
| EP0010697A1 (de) | 1980-05-14 |
| CA1122220A (en) | 1982-04-20 |
| IE49102B1 (en) | 1985-07-24 |
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