Sodium Hydroxide → N'-[6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidine

HRID 508464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508464
[CH2:1]([N:3]([CH3:6])[CH:4]=O)[CH3:2].[Cl-].[P+]=O.[Cl:10][C:11]1[CH:31]=[CH:30][C:14]([O:15][C:16]2[N:21]=[C:20]([CH3:22])[C:19]([NH2:23])=[CH:18][C:17]=2[C:24]#[C:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:13][C:12]=1[C:32]([F:35])([F:34])[F:33].[OH-].[Na+]>ClCCl>[Cl:10][C:11]1[CH:31]=[CH:30][C:14]([O:15][C:16]2[N:21]=[C:20]([CH3:22])[C:19]([N:23]=[CH:4][N:3]([CH2:1][CH3:2])[CH3:6])=[CH:18][C:17]=2[C:24]#[C:25][Si:26]([CH3:29])([CH3:27])[CH3:28])=[CH:13][C:12]=1[C:32]([F:34])([F:33])[F:35]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 350667N-ethyl-N-methylformamideHCID 581534926-(4-Chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-ylamineHCID 178527006HCID 178527006, Verbindung

Produkt 1

HCID 25159299N'-[6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-yl]-N-ethyl-N-methyl-formamidineAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In a 10 ml single-necked round-bottomed flask, 3.1 mg of ethylmethylformamide is solubilized in 0.25 ml of dry dichloromethane at ambient temperature (colourless solution). Under stirring, 0.0032 ml of phosphorous oxide chloride is added dropwise by syringe. Stirring at ambient temperature is continued for 1.0 hour, whereupon a pink-orange solution is obtained. To this solution, 7.0 mg of 6-(4-chloro-3-trifluoromethyl-phenoxy)-2-methyl-5-trimethylsilanylethynyl-pyridin-3-ylamine dissolved in 0.75 ml of dry dichloromethane is added dropwise by syringe, giving a yellow solution. Stirring is continued at room temperature for 2.5 hours. The mixture is then poured into ice/water (pH=2, water phase). 2 M aqueous NaOH is then added to get a pH of about 11 and stirring is continued for 15 minutes. The mixture is then extracted with two 10 ml portions of diethyl ether. The combined organic phases are then dried over sodium sulfate, filtered and the solvent is removed in vacuo to obtain 6.0 mg of the compound as a yellow oil. RP HPLC: retention time of compound: 1.61 minutes.

Aufarbeitung

  1. stirringStirring at ambient temperature
  2. customis obtained
  3. additionis added dropwise by syringe
  4. customgiving a yellow solution
  5. stirringStirring
  6. waitis continued at room temperature for 2.5 hours
  7. customto get a pH of about 11
  8. stirringstirring
  9. waitis continued for 15 minutes
  10. extractionThe mixture is then extracted with two 10 ml portions of diethyl ether
  11. dry with materialThe combined organic phases are then dried over sodium sulfate
  12. filtrationfiltered
  13. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9291f44c4d84dada4d88f213262603c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096525B2

Notizen zur Reaktion

Wird geladen…