PL435416A1 - Method for preparation of 1- (N-acylamino) alkyltriarylphosphonium salts - Google Patents
Method for preparation of 1- (N-acylamino) alkyltriarylphosphonium saltsInfo
- Publication number
- PL435416A1 PL435416A1 PL435416A PL43541620A PL435416A1 PL 435416 A1 PL435416 A1 PL 435416A1 PL 435416 A PL435416 A PL 435416A PL 43541620 A PL43541620 A PL 43541620A PL 435416 A1 PL435416 A1 PL 435416A1
- Authority
- PL
- Poland
- Prior art keywords
- general formula
- et2o
- alkyltriarylphosphonium
- acylamino
- salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 150000003951 lactams Chemical class 0.000 abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Abstract
Przedmiotem zgłoszenia jest sposób wytwarzania soli 1-(N-acyloamino)alkilotriarylofosfoniowych o wzorze ogólnym 1, w którym R1 oznacza Me, Ph, t-Bu, BnO; R2 oznacza H, Me, Et, Ph, i-Pr, 2-tienyl; R3 oznacza H, Me lub R1 i R3 razem oznaczają (CH2)3; Ar oznacza Ph, 3-C6H4Cl, 4-C6H4OMe; X oznacza BF4, Br, który polega na tym, że aldehydy o wzorze ogólnym 2, w którym R2 oznacza H, Me, Et, Ph, i-Pr, 2-tienyl; amidy, karbaminiany, lub laktamy o wzorze ogólnym 3, w którym R1 oznacza Me, Ph, t-Bu, BnO; R3 oznacza H, Me lub R1 i R3 razem oznaczają (CH2)3 oraz sole triarylofosfoniowe o wzorze ogólnym 4, w którym Ar oznacza Ph, 3-C6H4Cl, 4-C6H4OMe; X oznacza BF4, Br miesza się w stosunku molowym 1:1:1, aldehyd o wzorze ogólnym 2: amid/karbaminian/laktam o wzorze ogólnym 3: sól triarylofosfoniowa o wzorze ogólnym 4 lub miesza z nadmiarem aldehydu 1,2:1:0,9 w rozpuszczalnikach organicznych takich jak CH3CN, CHCl3, CH2Cl2, THF lub bez użycia rozpuszczalnika, przy czym proces prowadzi się w temperaturze 25° - 135°C, korzystnie w temperaturze 50°C, w czasie 1 – 48h, po czym surową sól 1-(N-acyloamino)alkilotriarylofosfoniową strąca się za pomocą Et2O lub heksanu, następnie korzystnie rekrystalizuje z CH3CN lub układów CHCl3/Et2O, CH3CN/Et2O, CH2Cl2/Et2O.The subject of the application is a process for the preparation of 1- (N-acylamino) alkyltriarylphosphonium salts of the general formula I, in which R1 is Me, Ph, t-Bu, BnO; R2 is H, Me, Et, Ph, i-Pr, 2-thienyl; R3 is H, Me or R1 and R3 together are (CH2) 3; Ar is Ph, 3-C6H4Cl, 4-C6H4OMe; X is BF4, Br, in which aldehydes of general formula II in which R2 is H, Me, Et, Ph, i-Pr, 2-thienyl; amides, carbamates or lactams of general formula 3 in which R 1 is Me, Ph, t-Bu, BnO; R3 is H, Me or R1 and R3 together are (CH2) 3 and triarylphosphonium salts of the general formula in which Ar is Ph, 3-C6H4Cl, 4-C6H4OMe; X is BF4, Br is mixed in a molar ratio of 1: 1: 1, aldehyde of general formula 2: amide / carbamate / lactam of general formula 3: triarylphosphonium salt of general formula 4 or mixed with excess aldehyde 1.2: 1: 0 , 9 in organic solvents such as CH3CN, CHCl3, CH2Cl2, THF or without the use of a solvent, the process is carried out at a temperature of 25 ° - 135 ° C, preferably at a temperature of 50 ° C, for 1-48 hours, then crude salt 1- (N-acylamino) alkyltriarylphosphonium is precipitated with Et2O or hexane, then preferably recrystallized from CH3CN or CHCl3 / Et2O, CH3CN / Et2O, CH2Cl2 / Et2O systems.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL435416A PL243696B1 (en) | 2020-09-22 | 2020-09-22 | Method for preparation of 1- (N-acylamino) alkyltriarylphosphonium salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL435416A PL243696B1 (en) | 2020-09-22 | 2020-09-22 | Method for preparation of 1- (N-acylamino) alkyltriarylphosphonium salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL435416A1 true PL435416A1 (en) | 2022-03-28 |
| PL243696B1 PL243696B1 (en) | 2023-10-02 |
Family
ID=80855563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL435416A PL243696B1 (en) | 2020-09-22 | 2020-09-22 | Method for preparation of 1- (N-acylamino) alkyltriarylphosphonium salts |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL243696B1 (en) |
-
2020
- 2020-09-22 PL PL435416A patent/PL243696B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL243696B1 (en) | 2023-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Nath et al. | A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine | |
| SA521421235B1 (en) | Formulations with an enhanced urease inhibitory effect comprising (thio)phosphoric acid triamide and other compounds such as amines and coloring agents. | |
| BR9003851A (en) | COATING COMPOSITES, PROCESS TO PRODUCE A COATING, SALTS AND PROCESS TO AVOID CORROSION IN METALLIC SURFACES | |
| KR960701018A (en) | Herbicidal heterocyclic-substituted pyridines | |
| Su et al. | Strontium (II) triflate catalysed condensation of β-naphthol, aldehyde and urea or amides: a facile synthesis of amidoalkyl naphthols | |
| JP4115546B2 (en) | Method for producing 1- (haloaryl) heterocyclic compound for agricultural chemicals | |
| HUP0002931A2 (en) | Process for the production of pesticide-active pyrazole derivatives and their intermediates, and the new starting materials and intermediates | |
| MX2023003173A (en) | A process for the synthesis of anthranilic acid/amide compounds and intermediates thereof. | |
| Ghosh et al. | An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine (III) reagent | |
| MX2024008480A (en) | Nitrogen-containing heterocyclic compound having nrf2 activation effect. | |
| CA2219359C (en) | Hydantoin derivatives as intermediates for pharmaceutical active compounds | |
| CZ320095A3 (en) | Process for preparing aminoalkyl guanidines | |
| PL435416A1 (en) | Method for preparation of 1- (N-acylamino) alkyltriarylphosphonium salts | |
| Bakulev et al. | Study of polyfunctional diazo compounds reactivity in heterocyclization by the method of intramolecular competitive reactions | |
| Dyachenko et al. | Synthesis and alkylation of new 3-functionally substituted carbo [c] fused pyridin-2-ones (thiones) | |
| ES2017950B3 (en) | NEW CHEMICAL PROCEDURE FOR THE OBTAINING OF OXAMIDE DERIVATIVES AND COMPOUNDS OBTAINED THROUGH THE SAME. | |
| Jochims et al. | The reaction of nitrilium salts with primary, secondary, and tertiary carboxamides | |
| RU2009123470A (en) | AGENT FOR INHIBITING THE SIGNAL FUNCTION OF CYTOKININ | |
| US4335247A (en) | Novel nitrosourea derivatives and process for their production | |
| Dalloul | Heterocyclic synthesis using Nitrile imines. 4. synthesis of 3-substituted 1-aryl-1, 2, 4-triazaspiroalk-2-enes | |
| Obi et al. | Synthesis of Novel Monobactams Bearing an (R)-1-Hydroxyethyl Group and an (S)-1-Carbamoyl-oxyethyl Group at the C3, 4-Positions | |
| Palacios et al. | SYNTHESIS OF N-FUNCTIONALIZED CARBODIIMIDES, HYDANTOINS, 1, 3-DIAZETIDINES, AND IMIDAZOLIDINE DERIVATIVES FROM N-VINYLIC PHOSPHAZENES DERIVED FROM ß-AMINO ACIDS | |
| GB1353789A (en) | Process for producing 2-n-monosubstituted amino-phenyl ketones and their conversion to quinazoline derivatives | |
| PL429257A1 (en) | Improved method of pyrrolo[3,2-b]pyrroles synthesis | |
| Harale et al. | Synthesis of 3-(substitutedthiocarbamide)-aniline derivatives from di-tert-butyl dicarbonate (BoC) protected 3-chloroaniline |