Bromine → 2-Methyl-6-phenoxy-benzothiazole

HRID 538618Notes

Reaction equation

HRID 538618 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[S:17])[CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr>C(Cl)Cl>[CH3:16][C:15]1[S:17][C:10]2[CH:9]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:13]=[CH:12][C:11]=2[N:14]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 59402779N-(4-Phenoxy-phenyl)-thioacetamide

Product 1

HCID 38382522-Methyl-6-phenoxy-benzothiazoleYield 10.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To an ice-cold solution of N-(4-phenoxy-phenyl)-thioacetamide (0.78 g, 3.20 mmol) in 10 ml of DCM was added Br2 (0.32 ml, 6.40 mmol) dropwise. The reaction mixture was heated at 45° C. for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated under reduced pressure. The residue was basified with NH4OH solution and extracted with ethyl acetate. The combined organics were, dried, (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica (230-400 M) using ethyl acetate/hexane (3:97) as the eluent to provide the title compound (0.08 g, 10.3%).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialdried, (Na2SO4),
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica (230-400 M)

Sources & evidence

ORD record
ord-e7eb54030e304037bbbc48ee6335c67e
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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