JP2013502391A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013502391A5 JP2013502391A5 JP2012525122A JP2012525122A JP2013502391A5 JP 2013502391 A5 JP2013502391 A5 JP 2013502391A5 JP 2012525122 A JP2012525122 A JP 2012525122A JP 2012525122 A JP2012525122 A JP 2012525122A JP 2013502391 A5 JP2013502391 A5 JP 2013502391A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfuric acid
- organic phase
- aqueous base
- reaction
- temperature
- 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.)
- Withdrawn
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000012074 organic phase Substances 0.000 claims description 11
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- CYMPUOGZUXAIMY-UHFFFAOYSA-N 4-methoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OC)=CC=C1NC1=CC=CC=C1 CYMPUOGZUXAIMY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- QPNFUBAIQZJEPO-UHFFFAOYSA-N 2-[4-(dibutylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QPNFUBAIQZJEPO-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09168288.0 | 2009-08-20 | ||
| EP09168288A EP2289896A1 (en) | 2009-08-20 | 2009-08-20 | Process for the manufacture of 3-dibutylamino-6-methyl-7-anilinofluoran |
| PCT/EP2010/061530 WO2011020726A1 (en) | 2009-08-20 | 2010-08-09 | Process for the manufacture of 3-dibutylamino-6-methyl-7-anilinofluoran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013502391A JP2013502391A (ja) | 2013-01-24 |
| JP2013502391A5 true JP2013502391A5 (enExample) | 2013-03-14 |
Family
ID=41314566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012525122A Withdrawn JP2013502391A (ja) | 2009-08-20 | 2010-08-09 | ３−ジブチルラミノ−６−メチル−７−アニリノフルオランの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120149918A1 (enExample) |
| EP (2) | EP2289896A1 (enExample) |
| JP (1) | JP2013502391A (enExample) |
| KR (1) | KR20120062795A (enExample) |
| CN (1) | CN102471348A (enExample) |
| WO (1) | WO2011020726A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105838105B (zh) * | 2016-04-23 | 2017-12-05 | 浙江鸿盛化工有限公司 | 一步法制备黑色荧烷类热压敏染料的方法 |
| CN112010868B (zh) * | 2020-09-02 | 2021-07-27 | 华烁科技股份有限公司 | 一种制备黑色可逆热致变色染料的方法 |
| CN114349765B (zh) * | 2022-01-21 | 2023-05-16 | 内蒙古源宏精细化工有限公司 | 2-苯氨基-3-甲基-6-二丁氨基荧烷高效绿色合成的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166350A (en) | 1989-06-10 | 1992-11-24 | Ciba-Geigy Corporation | Process for the manufacture of fluoran compounds |
| GB9827569D0 (en) | 1998-12-16 | 1999-02-10 | Ciba Geigy Ag | Heat sensitive recording material |
| WO2003035245A1 (en) | 2001-10-25 | 2003-05-01 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of microcapsules |
| JP5194526B2 (ja) * | 2007-04-06 | 2013-05-08 | コニカミノルタホールディングス株式会社 | 薄膜トランジスタの製造方法、画素アレイの製造方法 |
| CN101323619A (zh) * | 2007-06-12 | 2008-12-17 | 上海瑞年精细化工有限公司 | 荧烷类化合物的制造方法 |
-
2009
- 2009-08-20 EP EP09168288A patent/EP2289896A1/en not_active Ceased
-
2010
- 2010-08-09 JP JP2012525122A patent/JP2013502391A/ja not_active Withdrawn
- 2010-08-09 WO PCT/EP2010/061530 patent/WO2011020726A1/en not_active Ceased
- 2010-08-09 CN CN2010800367241A patent/CN102471348A/zh active Pending
- 2010-08-09 KR KR1020127007031A patent/KR20120062795A/ko not_active Ceased
- 2010-08-09 EP EP10742481A patent/EP2467386A1/en not_active Withdrawn
- 2010-08-09 US US13/391,130 patent/US20120149918A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5247728B2 (ja) | ベンズイミダゾール誘導体の製造方法 | |
| JP2012521377A5 (enExample) | ||
| TW201609695A (zh) | 用於製備３－（３－氯－１ｈ－吡唑－１－基）吡啶的方法（二） | |
| JP2011502923A5 (enExample) | ||
| JP2014533285A5 (enExample) | ||
| JP2012001634A5 (enExample) | ||
| JP2014507414A5 (enExample) | ||
| JP2018507858A5 (enExample) | ||
| JP2013502391A5 (enExample) | ||
| JP2013508368A5 (enExample) | ||
| JP2013216655A (ja) | ブロナンセリンの改善された調製方法 | |
| JP2013100237A5 (enExample) | ||
| JP2007520512A5 (enExample) | ||
| CN105399635B (zh) | 微波合成2‑硝基‑3’,4’,5’‑三氟‑1,1’‑联苯的方法 | |
| JP6228210B2 (ja) | フルボキサミン遊離塩基の精製方法およびそれを用いた高純度フルボキサミンマレイン酸塩の製造方法 | |
| JP7236598B2 (ja) | 酸性官能基のアルキル化方法 | |
| CN103896819B (zh) | 一种(s)-1-氯乙酰基吡咯烷-2-甲酰胺的制备方法 | |
| JP2016525094A5 (enExample) | ||
| JP2015515963A5 (enExample) | ||
| Mahecha-Mahecha et al. | On the way to potential antifungal compounds: synthesis and in vitro activity of 2-benzofuranylacetic acid amides | |
| JP2012513391A5 (enExample) | ||
| JP6554542B2 (ja) | ボロキシンを使用してハロゲン化アザインドール化合物を調製するための方法 | |
| RU2541545C2 (ru) | Способ получения гидрохлоридов аминов адамантанового ряда | |
| WO2012172563A3 (en) | Novel polymorphs of fosamprenavir calcium | |
| US7265238B2 (en) | Process for preparing methyl 4-(aminomethyl)benzoate |