Water → N-[6-(4-amino-2-fluorophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

HRID 2095770Notes

Reaction equation

HRID 2095770 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[S:11][C:7]=2[CH:6]=1.O.[Cl-].[NH4+]>C(O)C>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:19]=[CH:18][C:8]3[N:9]=[C:10]([NH:12][C:13]([CH:15]4[CH2:17][CH2:16]4)=[O:14])[S:11][C:7]=3[CH:6]=2)=[C:2]([F:1])[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58158566N-[6-(2-fluoro-4-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158640N-[6-(4-amino-2-fluorophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of N-[6-(2-fluoro-4-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (1.15 g, 3.07 mmol) in ethanol (50 mL)/water (10 mL) were added ammonium chloride (1.64 g, 30.7 mmol) and reduced iron (856 g, 15.3 mmol), and the mixture was heated under reflux for 4 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with a mixed solution of ethanol/water. The solvent was evaporated under reduced pressure, 1N aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted 3 times with ethyl acetate/tetrahydrofuran. The combined organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/diisopropyl ether and collected by filtration to give the title compound (644 mg, 61%) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. filtrationfiltered through celite
  4. washwashed with a mixed solution of ethanol/water
  5. customThe solvent was evaporated under reduced pressure, 1N aqueous sodium hydroxide solution
  6. additionwas added to the residue
  7. extractionthe mixture was extracted 3 times with ethyl acetate/tetrahydrofuran
  8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was evaporated under reduced pressure
  11. washthe residue was washed with ethyl acetate/diisopropyl ether
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a5cf193367464d35b504fab9c211b8e5
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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