Methyl iodide → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime

HRID 989224

Reaktionsgleichung

Reaktionsgleichung von HRID 989224
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH:19]=[N:20][OH:21])[C:3]=1[S:22]([CH3:24])=[O:23].[O-][CH2:26]C.[Na+].IC>C(O)C>[CH3:26][O:21][N:20]=[CH:19][C:4]1[C:3]([S:22]([CH3:24])=[O:23])=[C:2]([NH2:1])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 2723922Sodium ethoxideHCID 1363524165-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime

Produkt 1

HCID 545293625-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oximeAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime (0.15 g) in ethanol was added to a solution of sodium ethoxide (0.025 g) in ethanol at 20° C., followed by iodomethane (0.023 ml). The reaction was monitored by HPLC and over the next 24 hours three additional equivalents of iodomethane were added. The reaction mixture was then, concentrated and partitioned between dichloromethane and water. The organic layer was water-washed, dried (MgSO4) and concentrated. This was then combined with crude product from another identical preparation and chromatographed on a silica gel column, eluting with hexane/ethyl acetate, to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime (0.06 g) as a yellow solid m.p.80° C. Compound 17.

Aufarbeitung

  1. additionwere added
  2. concentrationconcentrated
  3. custompartitioned between dichloromethane and water
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThis was then combined with crude product from another identical preparation
  8. customchromatographed on a silica gel column
  9. washeluting with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e404aca62405486785ab5eaec48067c8
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638956B2

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