2-Methylbenzenesulfonic acid → dimethyl 1-(3-chloropyridin-2-yl)-1H-pyrazole-3,5-dicarboxylate

HRID 421552

Reaktionsgleichung

Reaktionsgleichung von HRID 421552
[C:1]1(C)C(S(O)(=O)=O)=CC=CC=1.N1([C:17](=[CH:27][C:28](=[O:30])C)[CH:18]([C:23]([O:25][CH3:26])=[O:24])C(OC)=O)CCCC1.[Cl:31][C:32]1[C:33]([NH:38][NH2:39])=[N:34][CH:35]=[CH:36][CH:37]=1.[OH2:40].C1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[Cl:31][C:32]1[C:33]([N:38]2[C:27]([C:28]([O:30][CH3:1])=[O:40])=[CH:17][C:18]([C:23]([O:25][CH3:26])=[O:24])=[N:39]2)=[N:34][CH:35]=[CH:36][CH:37]=1

Komponenten

6

Edukt 4

HCID 69252-Methylbenzenesulfonic acid2×HCID 5561003-Chloro-2-hydrazinylpyridineHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 66672553Dimethyl 2-pyrrolidino-4-oxo-2-pentenedicarboxylate

Produkt 1

HCID 66672641dimethyl 1-(3-chloropyridin-2-yl)-1H-pyrazole-3,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

One spatula tip of toluenesulphonic acid is added to a solution of 15.6 g (64.8 mmol) of dimethyl 2-pyrrolidino-4-oxo-2-pentenedicarboxylate and 20.4 g (64.8 mmol) of the toluenesulphonic acid salt of 3-chloro-2-pyridin-2-ylhydrazine in 84 ml of methanol and the mixture is heated at 50° C. for 5 h. It is then admixed with 12.3 g (64.8 mmol) of toluenesulphonic acid monohydrate and stirred initially at 50° C. for 1 h and under reflux for 1 h. After the mixture has cooled to 0° C., the precipitated crystals are filtered off with suction and filtration is carried out over silica gel (cyclohexane/ethyl acetate=1:1).

Aufarbeitung

  1. temperatureunder reflux for 1 h
  2. temperatureAfter the mixture has cooled to 0° C.
  3. filtrationthe precipitated crystals are filtered off with suction and filtration

Quellen und Nachweise

ORD-Eintrag
ord-41b673cd1d8144939bc1b6694508ac5f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101550B2

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