JP6219681B2 - フルオロアシル化アリールアミンを調製するための方法 - Google Patents
フルオロアシル化アリールアミンを調製するための方法 Download PDFInfo
- Publication number
- JP6219681B2 JP6219681B2 JP2013230286A JP2013230286A JP6219681B2 JP 6219681 B2 JP6219681 B2 JP 6219681B2 JP 2013230286 A JP2013230286 A JP 2013230286A JP 2013230286 A JP2013230286 A JP 2013230286A JP 6219681 B2 JP6219681 B2 JP 6219681B2
- Authority
- JP
- Japan
- Prior art keywords
- fluoroacyl
- alkyl
- arylamine
- aryl
- substituted
- 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 - Fee Related
Links
- 150000004982 aromatic amines Chemical class 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 4
- -1 aluminum trichloride Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000010936 aqueous wash Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000007603 infrared drying Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012806 monitoring device Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012475 sodium chloride buffer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/682,767 US8754260B2 (en) | 2012-11-21 | 2012-11-21 | Method for preparing fluoroacylated arylamine |
| US13/682,767 | 2012-11-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014101363A JP2014101363A (ja) | 2014-06-05 |
| JP2014101363A5 JP2014101363A5 (OSRAM) | 2017-01-12 |
| JP6219681B2 true JP6219681B2 (ja) | 2017-10-25 |
Family
ID=50728561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013230286A Expired - Fee Related JP6219681B2 (ja) | 2012-11-21 | 2013-11-06 | フルオロアシル化アリールアミンを調製するための方法 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US8754260B2 (OSRAM) |
| JP (1) | JP6219681B2 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9196840B2 (en) * | 2012-11-21 | 2015-11-24 | Xerox Corporation | Fluoroacylated arylamines |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202408A (en) | 1991-11-25 | 1993-04-13 | Xerox Corporation | Arylamine containing terpolymers with CF3 substituted moieties |
| JPH0761955A (ja) * | 1993-08-23 | 1995-03-07 | Fuji Xerox Co Ltd | 新規なベンジジン誘導体およびその製造方法 |
| JP4313916B2 (ja) * | 1999-01-08 | 2009-08-12 | オリヱント化学工業株式会社 | トリアリールアミンダイマーの製造方法 |
| JP5135777B2 (ja) * | 2006-11-27 | 2013-02-06 | コニカミノルタビジネステクノロジーズ株式会社 | 色素増感型光電変換素子及び色素増感型太陽電池 |
| US7652148B1 (en) | 2008-08-29 | 2010-01-26 | Xerox Corporation | Electrophilic aromatic substitution with diacyl imidazolium |
-
2012
- 2012-11-21 US US13/682,767 patent/US8754260B2/en not_active Expired - Fee Related
-
2013
- 2013-11-06 JP JP2013230286A patent/JP6219681B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20140142339A1 (en) | 2014-05-22 |
| US8754260B2 (en) | 2014-06-17 |
| JP2014101363A (ja) | 2014-06-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101403723B1 (ko) | 술포네이트계 화합물 및 이의 제조방법 | |
| TW201914987A (zh) | 聯萘化合物 | |
| CN110997645B (zh) | 奥扎尼莫德的制备方法 | |
| EA021726B1 (ru) | Способы получения соединений, являющихся пролекарствами ингибиторов присоединения вируса вич, и их интермедиатов | |
| JP5731256B2 (ja) | ６，６−（９−フルオレニリデン）−ジ（２−ナフトール）の結晶多形体及びその製造方法 | |
| JP6219681B2 (ja) | フルオロアシル化アリールアミンを調製するための方法 | |
| JP5508432B2 (ja) | トリフェニレンを調製するための工程 | |
| CN106977489A (zh) | 一种制备多取代占吨酮类衍生物的方法 | |
| CN106188046B (zh) | 一种碘促进的3-芳硫基咪唑并[1,5-a]N-杂环化合物的合成方法 | |
| JP6787331B2 (ja) | 酸ハライド溶液の製造方法、混合溶液、及びモノエステル化合物の製造方法 | |
| JP6530807B2 (ja) | インデノイソキノリン派生物の調製方法 | |
| RS59795B1 (sr) | Proces za pripremu 1-(3,5-dihlorofenil)-2,2,2-trifluoroetanona i njegovih derivata | |
| CN120476102A (zh) | 具有联萘骨架的二酯化合物的晶体及其制造方法 | |
| JP5380005B2 (ja) | ビスベンゾオキサジノン化合物の製造方法 | |
| JP2009269820A (ja) | かご型シロキサン化合物の製造方法 | |
| JP6809485B2 (ja) | 酸ハライド溶液の製造方法、及びモノエステル化合物の製造方法 | |
| JP5419545B2 (ja) | オルトエステル化合物の製造方法 | |
| JP4118645B2 (ja) | カリックス［４］アレーン誘導体混合物の製造方法 | |
| CN107501024B (zh) | 一种1,2-二碘代烯烃类化合物的合成方法 | |
| JP3979743B2 (ja) | 光学活性なビニルホスフィンオキシドの製造方法 | |
| JP6095129B2 (ja) | 光学異性体用分離剤 | |
| JP5036198B2 (ja) | フルオレン骨格含有フタルイミド類及びそれから誘導されるジアミン類 | |
| Dong | Synthesis of Asymmetric Heterocycle-Fused Indacenes for Organic Electronic Application | |
| JP6853086B2 (ja) | 芳香族化合物およびその製造方法 | |
| US11661407B2 (en) | Process for the preparation of pyrylium salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20140424 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20161104 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161122 |
|
| A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20161122 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170131 |
|
| A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20170228 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170314 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170518 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170627 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170828 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170905 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170928 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6219681 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |