JPS6116377B2 - - Google Patents
Info
- Publication number
- JPS6116377B2 JPS6116377B2 JP59059660A JP5966084A JPS6116377B2 JP S6116377 B2 JPS6116377 B2 JP S6116377B2 JP 59059660 A JP59059660 A JP 59059660A JP 5966084 A JP5966084 A JP 5966084A JP S6116377 B2 JPS6116377 B2 JP S6116377B2
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- alkali metal
- sodium
- water
- parts
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- -1 alkali metal salt Chemical class 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000004280 Sodium formate Substances 0.000 claims description 9
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 9
- 235000019254 sodium formate Nutrition 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000007519 polyprotic acids Polymers 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000033444 hydroxylation Effects 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WPDWOCRJBPXJFM-UHFFFAOYSA-N 2-bromo-1-phenylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CC=C1 WPDWOCRJBPXJFM-UHFFFAOYSA-N 0.000 description 1
- WLVPRARCUSRDNI-UHFFFAOYSA-N 2-hydroxy-1-phenyl-1-propanone Chemical compound CC(O)C(=O)C1=CC=CC=C1 WLVPRARCUSRDNI-UHFFFAOYSA-N 0.000 description 1
- VXXNSJDAKPSAPJ-UHFFFAOYSA-N 2-hydroxy-1-phenylethanone hydrate Chemical compound O.OCC(=O)C1=CC=CC=C1 VXXNSJDAKPSAPJ-UHFFFAOYSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 239000007788 liquid Substances 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
- C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
- C08J9/108—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond in a heterocyclic ring containing at least one carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/608,450 US4097671A (en) | 1975-08-28 | 1975-08-28 | Dihydrooxadiazinones and method for making |
| US608450 | 1975-08-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59210029A JPS59210029A (ja) | 1984-11-28 |
| JPS6116377B2 true JPS6116377B2 ( ) | 1986-04-30 |
Family
ID=24436562
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51101164A Expired JPS6037102B2 (ja) | 1975-08-28 | 1976-08-26 | ジヒドロオキサジアジノン |
| JP59059659A Pending JPS59210030A (ja) | 1975-08-28 | 1984-03-29 | ハロケトンの製造方法 |
| JP59059660A Granted JPS59210029A (ja) | 1975-08-28 | 1984-03-29 | ヒドロキシケトンの製造方法 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51101164A Expired JPS6037102B2 (ja) | 1975-08-28 | 1976-08-26 | ジヒドロオキサジアジノン |
| JP59059659A Pending JPS59210030A (ja) | 1975-08-28 | 1984-03-29 | ハロケトンの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US4097671A ( ) |
| JP (3) | JPS6037102B2 ( ) |
| AU (1) | AU509026B2 ( ) |
| DE (1) | DE2637771C2 ( ) |
| FR (3) | FR2345439A1 ( ) |
| GB (1) | GB1562617A ( ) |
| IT (1) | IT1076946B ( ) |
| MX (1) | MX144483A ( ) |
| NL (1) | NL188409C ( ) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097671A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Dihydrooxadiazinones and method for making |
| GB2045769B (en) * | 1979-03-27 | 1983-05-11 | Gen Electric | Thermoplastic foamable blends |
| EP0052442B1 (en) * | 1980-11-14 | 1985-09-11 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| ZA827641B (en) * | 1981-11-12 | 1983-09-28 | Ici Plc | Thiadiazine, oxadiazine and triazine derivatives which possess cardiotonic and/or antihypertensive activity |
| US4495185A (en) * | 1981-11-12 | 1985-01-22 | Imperial Chemical Industries, Plc | 1,2,4-Triazin-3(2H) ones |
| JPS5962578A (ja) * | 1982-10-04 | 1984-04-10 | Mitsui Toatsu Chem Inc | オキサジアジン誘導体およびそれを含有する医薬組成物 |
| US4543368A (en) * | 1984-11-09 | 1985-09-24 | General Electric Company | Foamable polyetherimide resin formulation |
| JPH0678262B2 (ja) * | 1986-06-26 | 1994-10-05 | ダイセル化学工業株式会社 | α−ヒドロキシケトン類の製法 |
| US4904702A (en) * | 1986-12-30 | 1990-02-27 | General Electric Company | Foamable engineering thermoplastic compositions |
| JP2008500389A (ja) * | 2004-05-21 | 2008-01-10 | ダウ グローバル テクノロジーズ インコーポレイティド | １，３−ジブロモアセトン、１，３−ジクロロアセトン及びエピクロロヒドリンの製造方法 |
| US11897867B2 (en) | 2017-08-04 | 2024-02-13 | Bayer Aktiengesellschaft | 6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives as PDE3A and PDE3B inhibitors for treating cancer |
| JOP20200024A1 (ar) * | 2017-08-04 | 2020-02-02 | Bayer Ag | مركبات ثنائي هيدروكساديازينون |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3378556A (en) * | 1966-09-23 | 1968-04-16 | Dow Chemical Co | 3, 4, 5, 6-tetrahydro-2-keto-6-phenyl-4, 4, 5-trimethyl-2h-1, 3, 4-oxadiazinium halides |
| US3377345A (en) * | 1966-09-23 | 1968-04-09 | Dow Chemical Co | Substituted 3, 4, 5, 6-tetrahydro-2h-1, 3, 4-oxadiazin-2-one compounds and method ofpreparation thereof |
| CH595363A5 ( ) * | 1973-12-19 | 1978-02-15 | Ciba Geigy Ag | |
| US4097425A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Thermoplastic formable blends, a foaming method and products made thereby |
| US4097671A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Dihydrooxadiazinones and method for making |
-
1975
- 1975-08-28 US US05/608,450 patent/US4097671A/en not_active Expired - Lifetime
-
1976
- 1976-07-30 GB GB31856/76A patent/GB1562617A/en not_active Expired
- 1976-08-21 DE DE2637771A patent/DE2637771C2/de not_active Expired
- 1976-08-24 AU AU17100/76A patent/AU509026B2/en not_active Expired
- 1976-08-25 FR FR7625715A patent/FR2345439A1/fr active Granted
- 1976-08-26 IT IT26567/76A patent/IT1076946B/it active
- 1976-08-26 JP JP51101164A patent/JPS6037102B2/ja not_active Expired
- 1976-08-27 NL NLAANVRAGE7609534,A patent/NL188409C/xx not_active IP Right Cessation
- 1976-08-27 MX MX166076A patent/MX144483A/es unknown
-
1977
- 1977-03-01 FR FR7705910A patent/FR2357518A1/fr active Granted
- 1977-03-01 FR FR7705909A patent/FR2357516A1/fr active Granted
- 1977-04-21 US US05/789,420 patent/US4160088A/en not_active Expired - Lifetime
- 1977-06-22 US US05/808,861 patent/US4158094A/en not_active Expired - Lifetime
-
1984
- 1984-03-29 JP JP59059659A patent/JPS59210030A/ja active Pending
- 1984-03-29 JP JP59059660A patent/JPS59210029A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2357516A1 (fr) | 1978-02-03 |
| US4160088A (en) | 1979-07-03 |
| DE2637771A1 (de) | 1977-03-10 |
| FR2357518A1 (fr) | 1978-02-03 |
| FR2357516B1 ( ) | 1980-02-22 |
| NL7609534A (nl) | 1977-03-02 |
| JPS59210029A (ja) | 1984-11-28 |
| MX144483A (es) | 1981-10-20 |
| US4097671A (en) | 1978-06-27 |
| FR2345439B1 ( ) | 1980-05-30 |
| FR2345439A1 (fr) | 1977-10-21 |
| JPS5236678A (en) | 1977-03-22 |
| DE2637771C2 (de) | 1985-03-21 |
| IT1076946B (it) | 1985-04-27 |
| NL188409C (nl) | 1992-06-16 |
| US4158094A (en) | 1979-06-12 |
| FR2357518B1 ( ) | 1982-07-09 |
| GB1562617A (en) | 1980-03-12 |
| AU1710076A (en) | 1978-03-02 |
| AU509026B2 (en) | 1980-04-17 |
| JPS6037102B2 (ja) | 1985-08-24 |
| JPS59210030A (ja) | 1984-11-28 |
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