Bromine → N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide

HRID 2190457Notes

Reaction equation

HRID 2190457 reaction equation
[S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:25]=[CH:24][C:9]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:25]2[CH:24]=[C:9]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[CH:14]=[CH:15][CH:16]=3)[CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 86655394N-[3-(4-aminophenoxy)phenyl]-2,2,2-trifluoroacetamide

Product 1

HCID 86655395N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a solution of potassium thiocyanate (17.5 g, 180.0 mmol) in acetic acid (130 mL) was added a solution of N-[3-(4-aminophenoxy)phenyl]-2,2,2-trifluoroacetamide (13.0 g, 43.9 mmol) in acetic acid (20 mL), and the mixture was stirred at room temperature for 15 min. To the obtained solution was added dropwise a solution of bromine (7.71 g, 48.2 mmol) in acetic acid (30 mL) at room temperature over 30 min or longer and, after the completion of the dropwise addition, the mixture was stirred at room temperature for 13 hr. The resulting yellow solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), and basified with 8N aqueous sodium hydroxide solution. The aqueous layer was separated, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (200 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (10.3 g, 66%) as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

Workup

  1. additionafter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 13 hr
  3. filtrationThe resulting yellow solid was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  6. customThe aqueous layer was separated
  7. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (200 mL) and saturated brine (50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bbd08704d21347018a500638a44836b9
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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