Acetic Anhydride → N-(3-benzoyl-5-bromo-thiophen-2-yl) acetamide

HRID 133545

반응식

HRID 133545 반응식
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[Br:15]N1C(=O)CCC1=O.[C:23]([O:26]C(=O)C)(=O)[CH3:24].CCN(CC)CC>CN(C1C=CN=CC=1)C>[C:7]([C:6]1[CH:5]=[C:4]([Br:15])[S:3][C:2]=1[NH:1][C:23](=[O:26])[CH3:24])(=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 644720(2-Aminothiophen-3-yl)(phenyl)methanone

생성물 1

HCID 16640231N-(3-benzoyl-5-bromo-thiophen-2-yl) acetamide수율 53.3%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

To a stirred solution of 1.00 g (4.92 mmol) of (2-amino-thiophen-3-yl)-phenyl-methanone (the preparation of which is described in example 20) in 20 ml CFCl2 at 0° C. was added 0.92 g (5.18 mmol) NBS (N-bromo succinimide) in one portion. After 10 minutes, 4.65 ml (49.2 mmol) of acetic anhydride, 0.68 ml (4.92 mmol) of Et3N and 0.30 g (2.45 mmol) of DMAP were added. Stirring was continued at RT for 2 hours, the mixture was poured onto water and extracted three times with CH2Cl2. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/CH2Cl2 1:1) afforded 0.85 g (53%) N-(3-benzoyl-5-bromo-thiophen-2-yl)-acetamide as a light brown solid. ES-MS m/e (%): 324, 326 (M+H+, 100).

후처리

  1. customat 0° C.
  2. waitwas continued at RT for 2 hours
  3. additionthe mixture was poured onto water
  4. extractionextracted three times with CH2Cl2
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7024b35b3d4e45ab9107f3a2c86fa6c9
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390903B2

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