2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide → 5-Acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide

HRID 2369595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369595
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[N:10]([S:22](=[O:27])(=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]=[C:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=1)=[O:8]>C1(C)C=CC=CC=1.C1COCC1.[NH4+].[Cl-]>[CH3:25][N:23]([CH3:24])[S:22]([N:10]1[C:9]([C:7](=[O:8])[CH3:1])=[CH:13][C:12]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:11]1)(=[O:26])=[O:27]

Komponenten

6

Edukt 2

HCID 866738982-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, Verbindung2×

Produkt 1

HCID 679600925-Acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel3×HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A 1.4M solution of methylmagnesium bromide in toluene and THF (3.88 mL, 5.43 mmol) was added to a solution of 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide (1.54 g, 4.17 mmol) in THF (20 mL) at −78° C. and under nitrogen. The mixture was stirred at −78° C. for 1 hour and then at room temperature for 16 hours. Then, a second portion of methylmagnesium bromide in toluene and THF (3.58 mL, 5.01 mmol) was added at 0° C. and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with a saturated solution of NH4Cl and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide (1.2 g, 89% yield) as a white solid.

Aufarbeitung

  1. waitat room temperature for 16 hours
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionextracted with AcOEt
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50)
  9. customThe desired fractions were collected
  10. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8b14aa4a40ab49e9ac33ab5d891ff32b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703946B2

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