Potassium Iodide → Ethyl 4-[N-(3-cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetate

HRID 1744579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744579
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[CH:19]=[N:20][NH:21][C:22]=2[CH3:23])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>O.C1(C)C=CC=CC=1.CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[C:22]([CH3:23])=[N:21][N:20]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:19]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2]

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22227878N-(3-Cyano-4-neopentyloxyphenyl)-5-methylpyrazole-4-carboxamide

Produkt 1

HCID 22228013Ethyl 4-[N-(3-cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetateAusbeute 22,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

N-(3-Cyano-4-neopentyloxyphenyl)-5-methylpyrazole-4-carboxamide (2.4 g), potassium carbonate (1.1 g), potassium iodide (1.4 g) and ethyl bromoacetate (1.4 g) were added to a mixed solvent of dimethylformamide (24 ml) and toluene (24 ml) and the mixture was stirred at 60° C. for 4 h. The reaction mixture was added into water, washed with dilute hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform). Methylene chloride was added to the obtained oily substance to allow crystallization. The crystals were recrystallized from a mixed solvent of methylene chloride-n-hexane to give the title compound (0.7 g), melting point: 240° C.

Aufarbeitung

  1. washwashed with dilute hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customafter which the solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform)
  5. additionMethylene chloride was added to the obtained oily substance
  6. customcrystallization
  7. customThe crystals were recrystallized from a mixed solvent of methylene chloride-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-8e84ce2ce74b432aa0657e6324214d87
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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