Acetic Anhydride → N-(3-bromobenzenesulfonyl)acetamide

HRID 1665781

反応式

HRID 1665781 の反応式
[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

参加物

6

反応物 2

HCID 7918Acetic AnhydrideHCID 27347653-Bromobenzene-1-sulfonamide

生成物 1

HCID 61216233N-(3-bromobenzenesulfonyl)acetamide収率 51%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-157cb84ef6224d1f859e492b0d13202b
出典データセット
uspto-grants-2011_10
特許番号
US08039491B2

関連ノート

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