Trityl chloride → Dimethyl 1-trityl-3,5-pyrazoledicarboxylate

HRID 236727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236727
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[NH:7][N:6]=1)=[O:4].[H-].[Na+].[H][H].[C:18]1([C:24](Cl)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O.O.CN(C=O)C>[C:18]1([C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:7]2[C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

8

Edukt 4

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 14844913,5-dimethyl 1H-pyrazole-3,5-dicarboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 12377531Dimethyl 1-trityl-3,5-pyrazoledicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 1.84 g. (10 mmol) of 3,5-pyrazoledicarboxylic acid dimethyl ester* in 15 ml. of DMF, stirred at 0° under argon, was added 480 mg. (10 mmol) of 50% NaH (suspension in mineral oil). After the evolution of hydrogen had ceased, 2.7 g. (10 mmol) of triphenylmethyl chloride in 20 ml. of DMF was added dropwise. The mixture was allowed to warm to room temperature, stirred 1.5 hours, poured into H2O, and the resulting precipitate filtered. After recrystallization from 2-ethoxyethanol-H2O, there was obtained the end product. The analytical sample was obtained as colorless needles by recrystallization from DMF-H2O; mp 212°-213.5°.

Aufarbeitung

  1. additionwas added 480 mg
  2. filtrationthe resulting precipitate filtered
  3. customAfter recrystallization from 2-ethoxyethanol-H2O
  4. customthere was obtained the end product

Quellen und Nachweise

ORD-Eintrag
ord-33f2f6c2ddd84ba9ae4205c636ff5b3b
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04157331

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