Hydrochloric Acid → N-(4-bromophenyl)-6-fluoro-1,3-benzothiazol-2-amine

HRID 2356796Notes

Reaction equation

HRID 2356796 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.Cl.O1CCOCC1>C(O)CCC>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[S:3][C:4]3[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78074-BromoanilineHCID 312751,4-DioxaneHCID 20498702-Chloro-6-fluorobenzothiazole

Product 1

HCID 7147099N-(4-bromophenyl)-6-fluoro-1,3-benzothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-chloro-6-fluoro-benzothiazole (0.65 g, 3.5 mmol) and 4-bromoaniline (0.61 g, 3.5 mmol) in n-butanol (6 mL) was heated at 60-70° C. under nitrogen to obtain a solution, to which 4 M HCl in dioxane (0.43 mL, 1.73 mmol) was slowly added dropwise. The reaction mixture was then heated at 90° C. for 18 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The resulting solid was triturated with ethanol and collected by filtration. This yielded 0.98 g (88%) of the title compound. LC/MS m/z 323.0 (MH+); retention time 3.74 min. 1H NMR (CD3OD) δ 7.10-7.30 (m, 1H), 7.39 (d, 1H), 7.45 (d, 2H), 7.58-7.61 (m, 3H).

Workup

  1. customto obtain a solution
  2. temperatureThe reaction mixture was then heated at 90° C. for 18 h
  3. temperatureUpon cooling to rt
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe resulting solid was triturated with ethanol
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-df6e815f275a40b09d1f73e697b122cb
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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