Acetic Anhydride → N-(3-bromobenzenesulfonyl)acetamide

HRID 39203

Reaktionsgleichung

Reaktionsgleichung von HRID 39203
[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12](=[O:14])[CH3:13])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 7918Acetic AnhydrideHCID 27347653-Bromobenzene-1-sulfonamide

Produkt 1

HCID 61216233N-(3-bromobenzenesulfonyl)acetamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Bromobenzenesulfonamide (470 mg, 2.0 mmol) was dissolved in pyridine (1 mL). To this solution was added DMAP (7.3 mg, 0.060 mmol) and then acetic anhydride (570 μL, 6.0 mmol). The reaction was stirred for 3 h at room temperature during which time the reaction changed from a yellow solution to a clear solution. The solution was diluted with ethyl acetate, and then washed with aqueous NH4Cl solution (×3) and water. The organic layer was dried over MgSO4 and concentrated. The resulting oil was triturated with hexanes and the precipitate was collected by filtration to obtain N-(3-bromophenylsulfonyl)-acetamide as a shiny white solid (280 mg, 51%). 1H NMR (400 MHz, DMSO-d6) δ 12.43 (s, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.96-7.90 (m, 2H), 7.61 (t, J=8.0 Hz, 1H), 1.95 (s, 3H); HPLC ret. time 1.06 min; ESI-MS 278.1 m/z (MH+).

Aufarbeitung

  1. washwashed with aqueous NH4Cl solution (×3) and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting oil was triturated with hexanes
  5. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-63a2ec6c447d4e18a1ffe336ff4d2000
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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