N-bromobutanimide → N-[5-(2-Bromo-thiophen-3-yl)-4-methyl-thiazol-2-yl]-acetamide

HRID 1360873Notes

Reaction equation

HRID 1360873 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:12][C:13](=[O:15])[CH3:14])[S:5][C:6]=1[C:7]1[CH:11]=[CH:10][S:9][CH:8]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[Br:16][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[C:6]1[S:5][C:4]([NH:12][C:13](=[O:15])[CH3:14])=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11993592N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamide

Product 1

HCID 86652439N-[5-(2-Bromo-thiophen-3-yl)-4-methyl-thiazol-2-yl]-acetamideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamide obtained in Step I as described above (3880 mg; 16.3 mmol; 1 eq) is dissolved in ACN (375 ml). N-bromosuccinimide (2898 mg; 16.3 mmol; 1 eq) is added and the resulting solution is stirred at room temperature for 30 minutes. Solvents are concentrated. Water is added and the desired product is extracted with EtOAc (3 times). Organic phases are washed with water (3 times) and dried over MgSO4, affording the title compound (5000 mg; 97%).

Workup

  1. concentrationSolvents are concentrated
  2. additionWater is added
  3. extractionthe desired product is extracted with EtOAc (3 times)
  4. washOrganic phases are washed with water (3 times)
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4cc5c5d4d6264d5fbcc18c1d7c84900b
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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