Hydrochloric Acid → N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine

HRID 9585

Reaction equation

HRID 9585 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[N:6]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1.Cl>CCCCO>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=3[N:6]=2)=[C:15]([F:20])[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1230504-Bromo-2-fluoroanilineHCID 20498602-Chloro-4-methylbenzothiazole

Product 1

HCID 23549342N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amineYield 89.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-chloro-4-methyl-1,3-benzothiazole (0.25 g, 1.36 mmol) in n-BuOH (8 mL) was added 4-bromo-2-fluoroaniline (0.52 g, 2.72 mmol) and HCl (4.0 M in dioxane, 0.5 mL). The reaction was heated at 90° C. overnight. Solvent was removed by rotary evaporation and 1 N aqueous HCl was added. The aqueous layer was separated and extracted with EtOAc. The combined organic phases were washed with 1 N aqueous HCl and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was brought up in MeOH and the precipitate was collected by filtration, washed with MeOH, and dried in a vacuum oven to give N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine (0.41 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 7.07 (t, 1H), 7.15 (d, 1H), 7.36 (m, 2H), 7.51 (d, 1H), 8.72 (t, 1H).

Workup

  1. customSolvent was removed by rotary evaporation and 1 N aqueous HCl
  2. additionwas added
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic phases were washed with 1 N aqueous HCl and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with MeOH
  11. customdried in a vacuum oven

Sources & evidence

ORD record
ord-3859a45296554bedb58e00427182e1ee
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Linked notes

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