Acetic Anhydride → HCID 16640231、化合物

HRID 133545

反応式

HRID 133545 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 16640231HCID 16640231、化合物収率 53.3%

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7024b35b3d4e45ab9107f3a2c86fa6c9
出典データセット
uspto-grants-2008_06
特許番号
US07390903B2

関連ノート

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