Bromine → N-(4-bromo-2-methylthiazol-5-yl)acetamide

HRID 1051426Notes

Reaction equation

HRID 1051426 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

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

  1. customto give a brown solution
  2. extractionThe aqueous layer was extracted with DCM (3×30 mL)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a yellow solid
  7. 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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