Bromine → N-(4-bromo-2-methylthiazol-5-yl)acetamide
Reaction equation
[CH3:1][C:2]1[S:3][C:4]([NH:7][C:8](=[O:10])[CH3:9])=[CH:5][N:6]=1.[Br:11]Br>C(Cl)(Cl)Cl.OS([O-])=O.[Na+]>[Br:11][C:5]1[N:6]=[C:2]([CH3:1])[S:3][C:4]=1[NH:7][C:8](=[O:10])[CH3:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-(2-methylthiazol-5-yl)acetamide (0.4 g, 2.6 mmol) in CHCl3 (30 mL) was added Br2 (0.15 mL, 2.8 mmol), then the solution was stirred at room temperature for 12 h to give a brown solution. The reaction mixture was diluted with saturated NaHSO3 solution. The aqueous layer was extracted with DCM (3×30 mL). The combined organic layers were dried with Na2SO4, filtered and concentrated to afford a yellow solid. The resulting mixture was deposited onto silica gel and loaded onto a silica gel column and eluted with PE/EA(1:1) to give the title compound (400 mg, yield 67%).
Workup
- customto give a brown solution
- extractionThe aqueous layer was extracted with DCM (3×30 mL)
- dry with materialThe combined organic layers were dried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto afford a yellow solid
- washeluted with PE/EA(1:1)
Sources & evidence
- ORD record
- ord-432fd5a06d8249868afbdf458b1a3e7c
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388180B2
Reaction notes
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