JPS6121942B2 - - Google Patents
Info
- Publication number
- JPS6121942B2 JPS6121942B2 JP53031646A JP3164678A JPS6121942B2 JP S6121942 B2 JPS6121942 B2 JP S6121942B2 JP 53031646 A JP53031646 A JP 53031646A JP 3164678 A JP3164678 A JP 3164678A JP S6121942 B2 JPS6121942 B2 JP S6121942B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen peroxide
- general formula
- added
- derivative represented
- reaction
- 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000007857 hydrazones Chemical class 0.000 claims description 8
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
- 150000002497 iodine compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000011229 interlayer Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 description 5
- -1 iodine, alkali metal salts Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 4
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 4
- 235000004279 alanine Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229910021543 Nickel dioxide Inorganic materials 0.000 description 1
- MUEYUJPOPWNQQT-UHFFFAOYSA-L [OH-].C(C1=CC=CC=C1)[N+](C)(C)C.[OH-].C(C1=CC=CC=C1)[N+](C)(C)C Chemical compound [OH-].C(C1=CC=CC=C1)[N+](C)(C)C.[OH-].C(C1=CC=CC=C1)[N+](C)(C)C MUEYUJPOPWNQQT-UHFFFAOYSA-L 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- WFEXFNMTEBFLMM-UHFFFAOYSA-M trioctyl(propyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCC)(CCCCCCCC)CCCCCCCC WFEXFNMTEBFLMM-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3164678A JPS54125620A (en) | 1978-03-22 | 1978-03-22 | Preparation of diazomethane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3164678A JPS54125620A (en) | 1978-03-22 | 1978-03-22 | Preparation of diazomethane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54125620A JPS54125620A (en) | 1979-09-29 |
| JPS6121942B2 true JPS6121942B2 (enrdf_load_stackoverflow) | 1986-05-29 |
Family
ID=12336946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3164678A Granted JPS54125620A (en) | 1978-03-22 | 1978-03-22 | Preparation of diazomethane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54125620A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01131131U (enrdf_load_stackoverflow) * | 1988-03-01 | 1989-09-06 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632397B (zh) * | 2016-12-01 | 2019-03-22 | 齐鲁天和惠世制药有限公司 | 一种6α-溴青霉烷-3α-羧酸二苯甲酯-1β-氧化物的制备方法 |
-
1978
- 1978-03-22 JP JP3164678A patent/JPS54125620A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01131131U (enrdf_load_stackoverflow) * | 1988-03-01 | 1989-09-06 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54125620A (en) | 1979-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU177591B (en) | Process for producing 1-methyl-10-methoxy-lumilizergole derivatives | |
| JPS6121942B2 (enrdf_load_stackoverflow) | ||
| JPS62169755A (ja) | テトラクロロ−２−シアノ安息香酸アルキルエステルの製造方法 | |
| JPS6249261B2 (enrdf_load_stackoverflow) | ||
| JPS6024781B2 (ja) | シス−２−ヒドロキシ−２−フエニル−ｒ−１−シクロヘキサンカルボン酸の製造法 | |
| JPH07121944B2 (ja) | Ｎ▲下１▼‐メチル‐１０α‐メトキシルミリセルゴールの製造方法 | |
| JPS6087251A (ja) | 置換ベンズアミド誘導体の製造法 | |
| JPH06298683A (ja) | 光反応による４−（２−置換）フェニルベンジルブロミド類の製造法 | |
| JP2743198B2 (ja) | シクロペンタン類 | |
| JPH03170451A (ja) | クロロフタル酸化合物からの塩素の選択的除去方法 | |
| JPH0478638B2 (enrdf_load_stackoverflow) | ||
| JPS58216159A (ja) | キノリン誘導体の製造方法 | |
| JPS626552B2 (enrdf_load_stackoverflow) | ||
| JP2706554B2 (ja) | ４―トリフルオロメチルアニリン誘導体及びその製造法 | |
| CA1233823A (en) | Process for the production of 4-substituted acetoacetic acid derivatives | |
| JPH04330045A (ja) | デアセチルコルヒチンの製造方法 | |
| JPS6130556A (ja) | ２，４，６−トリフルオロ安息香酸の製造方法 | |
| JPH0788344B2 (ja) | 芳香族ジアゾ化合物の製法 | |
| JPH0662539B2 (ja) | ２，３−ジシアノ−１，４−ジヒドロキシナフタレン誘導体の製造方法 | |
| CN113292414A (zh) | 一种丁炔二酸的制备方法 | |
| JP3167811B2 (ja) | １Ｒ，ｃｉｓ−２，２−ジメチル−３−ホルミルシクロプロパン−１−カルボン酸のラクトンの新製造法及び中間体 | |
| JPH0354665B2 (enrdf_load_stackoverflow) | ||
| JPH0338549A (ja) | 置換レゾルシン酸エステル類の製造法 | |
| JPH0316342B2 (enrdf_load_stackoverflow) | ||
| JPS6031826B2 (ja) | 置換酢酸誘導体の製法 |