Methyl iodide → Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetate

HRID 81861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81861
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.O>[CH3:17][N:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetate

Produkt 1

HCID 3277444Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-(4-methylphenylsulfonamido)acetate (3.10 g, 12.8 mmol) and Cs2CO3 (8.31 g, 25.5 mmol) in DMF (0.1 M) was added MeI (877 μL, 14.1 mmol). The reaction was allowed to stir overnight at rt. The reaction was then diluted with water and repeatedly extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to furnish 6 (2.80 g, 85%): δH (400 MHz, CDCl3) 2.42 (s, 3H, CH3), 2.87 (s, 3H, CH3), 3.66 (s, 3H, CH3), 3.97 (s, 2H, CH2), 7.31 (d, J=8.4 Hz, 2H, CH), 7.69 (d, J=8.4 Hz, 2H, CH); LRMS (ES+) calcd for [C11H15NO4S+H] 258.08. found 258.06 [M+H].

Aufarbeitung

  1. extractionrepeatedly extracted with CH2Cl2
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d4b828cd64a8417780dcb6b0c0dc101b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846707B2

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