Acetic Anhydride → N-(3-bromobenzenesulfonyl)acetamide

HRID 39203

반응식

HRID 39203 반응식
[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

참가 물질

6

반응물 2

HCID 7918Acetic AnhydrideHCID 27347653-Bromobenzene-1-sulfonamide

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-63a2ec6c447d4e18a1ffe336ff4d2000
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524767B2

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