Acetic Anhydride → HCID 16640231, compound

HRID 133545

Reaction equation

HRID 133545 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 16640231HCID 16640231, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7024b35b3d4e45ab9107f3a2c86fa6c9
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Linked notes

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