JP2014512346A - s−トリアジン化合物の調製方法 - Google Patents
s−トリアジン化合物の調製方法 Download PDFInfo
- Publication number
- JP2014512346A JP2014512346A JP2014500522A JP2014500522A JP2014512346A JP 2014512346 A JP2014512346 A JP 2014512346A JP 2014500522 A JP2014500522 A JP 2014500522A JP 2014500522 A JP2014500522 A JP 2014500522A JP 2014512346 A JP2014512346 A JP 2014512346A
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- JP
- Japan
- Prior art keywords
- reaction
- process according
- solvent
- acid halide
- cyanuric acid
- 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.)
- Granted
Links
- -1 s-triazine compound Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229960004050 aminobenzoic acid Drugs 0.000 claims abstract description 12
- 150000003738 xylenes Chemical class 0.000 claims abstract description 9
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 125000003158 alcohol group Chemical group 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 230000003711 photoprotective effect Effects 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FHNYFUNJQHPHAC-UHFFFAOYSA-N 2h-triazin-5-one Chemical compound OC1=CN=NN=C1 FHNYFUNJQHPHAC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- ZJQXUTDROPGVLH-UHFFFAOYSA-N 2-ethylhexyl 4-aminobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N)C=C1 ZJQXUTDROPGVLH-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 1
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- YOIYKKLGDLFRMF-UHFFFAOYSA-N 8-ethyldodecan-6-ol Chemical compound CCCCCC(O)CC(CC)CCCC YOIYKKLGDLFRMF-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- IKNFJAZOUAIWGX-UHFFFAOYSA-N CCCCCC(CC)C(c(cc1)ccc1Nc1nc(Nc(cc2)ccc2C(CC(CC)CCCC)=O)nc(Nc(cc2)ccc2C(CC(CC)CCCC)=O)n1)=O Chemical compound CCCCCC(CC)C(c(cc1)ccc1Nc1nc(Nc(cc2)ccc2C(CC(CC)CCCC)=O)nc(Nc(cc2)ccc2C(CC(CC)CCCC)=O)n1)=O IKNFJAZOUAIWGX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KTAQORMASMTUAT-UHFFFAOYSA-N octan-3-yl 4-aminobenzoate Chemical compound CCCCCC(CC)OC(=O)C1=CC=C(N)C=C1 KTAQORMASMTUAT-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
750mLのフラスコ中に、147gのp-アミノ安息香酸エチルヘキシルを、初期仕込み物として75mLのキシレンと共に導入し、120℃まで加熱する。1時間にわたって、37.5gの塩化シアヌルを、撹拌しながら115℃〜125℃で計量供給し、続いて37mLのキシレンで洗い落す。約120℃で1時間にわたって後反応を行う。約90℃まで冷却した後、混合物を、塩化ナトリウム溶液を用いて中性とし、続いて30分間撹拌する。
Claims (9)
- キシレン異性体混合物が、反応の開始に先立って共沸脱水されることを特徴とする、請求項1又は2に記載の方法。
- 反応が、溶媒なしで実施されることを特徴とする、請求項1から3のいずれか一項に記載の方法。
- 反応が、85〜140℃の温度で実施されることを特徴とする、請求項1から4のいずれか一項に記載の方法。
- p-アミノ安息香酸エステルが、化学量論的に添加されることを特徴とする、請求項1から5のいずれか一項に記載の方法。
- シアヌル酸ハライドが、共沸脱水されたキシレン異性体混合物との懸濁液として使用されることを特徴とする、請求項1から6のいずれか一項に記載の方法。
- 反応容器に付着しているシアヌル酸ハライドが、加圧下にて前記溶媒を用いて操作される回転洗浄ノズルを使用して除去されることを特徴とする、請求項7に記載の方法。
- 真空蒸留によって精製されたp-アミノ安息香酸エステルが、脱水されたキシレン異性体混合物を含む反応器中に導入され、80〜110℃まで加熱され、次いでシアヌル酸ハライドの懸濁液が、110〜120℃の温度で計量供給されることを特徴とする、請求項1から8のいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161466481P | 2011-03-23 | 2011-03-23 | |
EP11159352.1 | 2011-03-23 | ||
EP11159352 | 2011-03-23 | ||
US61/466481 | 2011-03-23 | ||
PCT/IB2012/051344 WO2012127425A1 (en) | 2011-03-23 | 2012-03-21 | Process for the preparation of s-triazine compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014512346A true JP2014512346A (ja) | 2014-05-22 |
JP6066986B2 JP6066986B2 (ja) | 2017-01-25 |
Family
ID=44064612
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014500522A Active JP6066986B2 (ja) | 2011-03-23 | 2012-03-21 | s−トリアジン化合物の調製方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8765753B2 (ja) |
EP (1) | EP2688875B1 (ja) |
JP (1) | JP6066986B2 (ja) |
KR (1) | KR101859249B1 (ja) |
CN (1) | CN103443086B (ja) |
BR (1) | BR112013023786B1 (ja) |
ES (1) | ES2560019T3 (ja) |
WO (1) | WO2012127425A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016044821A1 (en) * | 2014-09-19 | 2016-03-24 | Children's Medical Center Corporation | Apparatuses for cleaning catheter ports |
CN104860893B (zh) * | 2015-04-13 | 2017-07-11 | 三峡大学 | 一种紫外线吸收剂辛基三嗪酮的合成方法 |
US10472594B2 (en) * | 2017-04-11 | 2019-11-12 | Itaconix Corporation | Sulfonated copolymers for detergent composition |
CN106986839B (zh) * | 2017-04-28 | 2018-02-27 | 湖北师范大学 | 一种紫外线吸收剂uvt‑150的制备方法 |
CN112321522B (zh) * | 2020-09-09 | 2022-06-28 | 马鞍山科思化学有限公司 | 一种防晒剂辛基三嗪酮的制备方法 |
WO2024046956A1 (en) * | 2022-08-29 | 2024-03-07 | Basf Se | Improved process for preparing s-triazine derivatives |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58157774A (ja) * | 1982-02-23 | 1983-09-19 | バスフ アクチエンゲゼルシヤフト | s−トリアジン誘導体及びその光保護剤としての使用 |
JPS61271281A (ja) * | 1985-05-24 | 1986-12-01 | バスフ アクチェン ゲゼルシャフト | S−トリアジン誘導体の製法 |
JP2000063388A (ja) * | 1998-01-02 | 2000-02-29 | F Hoffmann La Roche Ag | 光遮蔽組成物としてのシラニル―トリアジン |
JP2012510492A (ja) * | 2008-12-03 | 2012-05-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺害虫剤及びuv吸収剤を含んでいる農薬組成物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4382308A (en) | 1981-02-18 | 1983-05-10 | Chemcut Corporation | Scrubbing torque monitoring and control system |
EP2222908B1 (en) | 2007-12-06 | 2013-01-16 | 3M Innovative Properties Company | Electret webs with charge-enhancing additives |
CN101525317A (zh) | 2009-03-20 | 2009-09-09 | 孙玉明 | 一种辛基三嗪酮及其互变异构体的制备工艺 |
-
2012
- 2012-03-21 KR KR1020137027518A patent/KR101859249B1/ko active IP Right Grant
- 2012-03-21 WO PCT/IB2012/051344 patent/WO2012127425A1/en active Application Filing
- 2012-03-21 EP EP12759876.1A patent/EP2688875B1/en active Active
- 2012-03-21 JP JP2014500522A patent/JP6066986B2/ja active Active
- 2012-03-21 US US14/004,180 patent/US8765753B2/en not_active Expired - Fee Related
- 2012-03-21 ES ES12759876.1T patent/ES2560019T3/es active Active
- 2012-03-21 CN CN201280014574.3A patent/CN103443086B/zh active Active
- 2012-03-21 BR BR112013023786-4A patent/BR112013023786B1/pt active IP Right Grant
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58157774A (ja) * | 1982-02-23 | 1983-09-19 | バスフ アクチエンゲゼルシヤフト | s−トリアジン誘導体及びその光保護剤としての使用 |
JPS61271281A (ja) * | 1985-05-24 | 1986-12-01 | バスフ アクチェン ゲゼルシャフト | S−トリアジン誘導体の製法 |
JP2000063388A (ja) * | 1998-01-02 | 2000-02-29 | F Hoffmann La Roche Ag | 光遮蔽組成物としてのシラニル―トリアジン |
JP2012510492A (ja) * | 2008-12-03 | 2012-05-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺害虫剤及びuv吸収剤を含んでいる農薬組成物 |
Non-Patent Citations (1)
Title |
---|
JPN6015053053; RICCI,A. et al: Photochemistry and Photobiology Vol.81, Iss.4, 2005, pp.949-952 * |
Also Published As
Publication number | Publication date |
---|---|
US20140005387A1 (en) | 2014-01-02 |
WO2012127425A1 (en) | 2012-09-27 |
EP2688875A4 (en) | 2014-09-17 |
CN103443086B (zh) | 2016-04-13 |
CN103443086A (zh) | 2013-12-11 |
BR112013023786B1 (pt) | 2019-04-30 |
EP2688875B1 (en) | 2015-12-30 |
JP6066986B2 (ja) | 2017-01-25 |
BR112013023786A2 (pt) | 2016-08-09 |
ES2560019T3 (es) | 2016-02-17 |
US8765753B2 (en) | 2014-07-01 |
KR101859249B1 (ko) | 2018-06-28 |
KR20140016945A (ko) | 2014-02-10 |
EP2688875A1 (en) | 2014-01-29 |
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