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

HRID 1948414Notes

Reaction equation

HRID 1948414 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-76573bf97d3848dcbf81621ed2183f9c
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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