Tetrahydrofuran → 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide

HRID 2369594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369594
C([Mg]Cl)(C)C.C1COCC1.C(O[C:14]([C:16]1[N:17]([S:29](=[O:34])(=[O:33])[N:30]([CH3:32])[CH3:31])[N:18]=[C:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=1)=[O:15])C.Cl.[CH3:36][NH:37][O:38][CH3:39]>C(Cl)Cl.[NH4+].[Cl-]>[CH3:39][O:38][N:37]([CH3:36])[C:14]([C:16]1[N:17]([S:29](=[O:33])(=[O:34])[N:30]([CH3:31])[CH3:32])[N:18]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=1)=[O:15]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 67958277HCID 67958277, VerbindungHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 866738982-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A 2M solution of isopropylmagnesium chloride in THF (1.9 mL, 3.8 mmol) was added to a stirred suspension of 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.45 g, 1.27 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.16 g, 1.65 mmol) in DCM (6.5 mL) under nitrogen at −78° C. The mixture was slowly allowed to warm to room temperature and stirred for 16 hours. The mixture was diluted with a saturated solution of NH4Cl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide (0.2 g, 44% yield) as a colourless oil that solidified upon standing.

Aufarbeitung

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents were evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-10c9f885dec746f396a1e1e4914d1f5e
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703946B2

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