Methanol → N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]acetamide

HRID 2190459Notes

Reaction equation

HRID 2190459 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[C:17]([NH:21]C(=O)C(F)(F)F)[CH:18]=[CH:19][CH:20]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].CO.O.O.[OH-].[Li+]>O1CCCC1.C(OCC)(=O)C>[NH2:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][C:12]1[CH:11]=[CH:10][C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=2[CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 86655396HCID 86655396, compound

Product 1

HCID 86655397N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]acetamideYield 41%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{[2-(acetylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide (10.0 g, 25.3 mmol) in tetrahydrofuran (50 mL) were added methanol (25 mL), water (25 mL) and lithium hydroxide monohydrate (1.50 g, 35.7 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added water (200 mL) and ethyl acetate (250 mL), and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100), and triturated with ethyl acetate/hexane to give the title compound (3.10 g, 41%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100)
  5. customtriturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-36fa751aecd74b4bad5215dddd0a7215
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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