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Pyridine → 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylate

HRID 2424322
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2424322
[CH3:1][C:2]1[NH:3][C:4]([CH3:7])=[CH:5][CH:6]=1.N1C=CC=CC=1.[C:14](Cl)(Cl)=[O:15].C1(C)C=CC=CC=1.[Cl:25][C:26]1[N:31]=[N:30][C:29]([O:32][C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH:40]2[CH2:42][CH2:41]2)=[C:28]([OH:43])[CH:27]=1>O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:14]([O:43][C:28]2[CH:27]=[C:26]([Cl:25])[N:31]=[N:30][C:29]=2[O:32][C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH:40]2[CH2:42][CH2:41]2)=[O:15])[C:4]([CH3:7])=[CH:5][CH:6]=1
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Komponenten

7

Edukt 4

HCID 1049Pyridine2×HCID 122652,5-DimethylpyrroleHCID 19083224Phosgen tolueneHCID 178424441HCID 178424441, Verbindung

Produkt 1

HCID 230138946-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylateAusbeute 16,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

37.4 mg (0.393 mmol) of 2,5-dimethyl-1H-pyrrole was mixed with toluene (1 mL), 40.0 ìL (0.407 mmol) of pyridine, then 0.34 mL (0.367 mmol) of 1.08 mol/L phosgene-toluene solution were added to the mixture in an ice bath with stirring, and the resulting mixture was stirred for 1 hour. To the mixture were added 40.0 ìL (0.407 mmol) of pyridine, then 100 mg (0.361 mmol) of 6-chloro-3-(2-cyclo-propyl-6-methylphenoxy)-4-pyridazinol, and the resulting mixture was stirred for 3 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 2 plates were used, developed by hexane:ethyl acetate=2:1) to obtain 24.0 mg (0.0603 mmol, Yield: 16.7%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylate (Compound No. 3630).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 2 plates were used, developed by hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f911c90b9644639afe8dd5920a47dc1
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07964531B2

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