4-tert-Butylphenoxyacetyl chloride → 2-(4-tert-Butylphenoxy)-N-{4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350832
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[C:15]([C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][C:25](Cl)=[O:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>N1C=CC=CC=1>[C:15]([C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][C:25]([NH:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=2)=[O:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

4

Edukt 2

HCID 6111954-tert-Butylphenoxyacetyl chlorideHCID 27609964-(Methylsulfonylamino)benzylamine hydrochloride

Produkt 1

HCID 210974732-(4-tert-Butylphenoxy)-N-{4-[(methylsulfonyl)amino]benzyl}acetamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred pyridine (15 ml) suspension of N-[4-(aminomethyl)-phenyl]methane sulfonamide hydrochloride (376 mg, 1.59 mmol) was added (4-tert-butylphenoxy)acetic acid chloride (300 mg, 1.3 mmol) at 0° C. and the mixture was stirred for 1 hour at ambient temperature. The reaction was then partitioned with ethylacetate and 2M aqueous solution of hydrogen chloride and the organic layer was separated, washed with brine, dried over magnesium sulfate. Then, filtration to remove magnesium sulfate, evaporation under reduced pressure gave the residue, which was applied to a silica gel chromatography column and eluted with a volume mixture of hexane/ethylacetate (1/1 to 1/2) to furnish 240 mg (62% yield) of title compound as a white solid.

Aufarbeitung

  1. customThe reaction was then partitioned with ethylacetate and 2M aqueous solution of hydrogen chloride
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThen, filtration
  6. customto remove
  7. custommagnesium sulfate, evaporation under reduced pressure
  8. customgave the residue, which
  9. washeluted with a volume mixture of hexane/ethylacetate (1/1 to 1/2)

Quellen und Nachweise

ORD-Eintrag
ord-5fd021b3f8ac4d209bdb3045e6c68dbe
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214824B2

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