Bromine → 2-Amino-6-(4-fluorophenoxy)benzothiazole

HRID 9127

Reaction equation

HRID 9127 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:16]([S-:18])#[N:17].[K+].BrBr>C(O)(=O)C>[NH2:17][C:16]1[S:18][C:12]2[CH:13]=[C:7]([O:6][C:5]3[CH:14]=[CH:15][C:2]([F:1])=[CH:3][CH:4]=3)[CH:8]=[CH:9][C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 147633Benzenamine, 4-(4-fluorophenoxy)-HCID 516872Potassium thiocyanate

Product 1

HCID 219855122-Amino-6-(4-fluorophenoxy)benzothiazoleYield 103.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 4-(4′-fluorophenoxy)aniline (0.305 g, 1.50 mmol) and KSCN (0.29 g, 3.00 mmol, 2.0 eq) in 3 mL acetic acid was cooled at about 5° C., and was treated dropwise with a solution of bromine (0.077 mL, 1.50 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 2 hours. The precipitate was filtered off and washed with Et2O. The mother liquid from the filtration was concentrated, and the residue was combined with the precipitate. The obtained solid was neutralized with saturated sodium carbonate solution, and a new precipitate was formed. It was filtered off, washed with water, and dried under vacuum to give the desired compound 0.403 g (90%). LC/MS 261.2 (M+1); LC retention time 2.44 min.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with Et2O
  3. filtrationThe mother liquid from the filtration
  4. concentrationwas concentrated
  5. customa new precipitate was formed
  6. filtrationIt was filtered off
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-39cabe140ee74440b053a8e259355b3d
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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