Lithium hydroxide, monohydrate → N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide

HRID 455179

Reaction equation

HRID 455179 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]#[N:15])=[C:12]([O:16][C:17]3[CH:18]=[C:19]([NH:23]C(=O)C(F)(F)F)[CH:20]=[CH:21][CH:22]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O.C(OCC)(=O)C>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][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[C:13]=1[C:14]#[N:15]

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86644687N-(3-{[2-(Acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 86644686N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamideYield 38.1%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-(3-{[2-(Acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide (6.8 g, 16.2 mmol) was dissolved in a mixed solvent of tetrahydrofuran (75 mL)/methanol (25 mL)/water (25 mL), lithium hydroxide monohydrate (1.99 g, 48.5 mmol) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with ethyl acetate (600 mL) and tetrahydrofuran (200 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was suspended in N,N-dimethylformamide/ethyl acetate (1:1), and the insoluble material was collected by filtration to give the title compound (2.00 g, 38%) as a white powder.

Workup

  1. additionwas added
  2. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationInsoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. filtrationthe insoluble material was collected by filtration

Sources & evidence

ORD record
ord-0bdc90c51b1e440aa85823e68eb7cc67
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Linked notes

Loading…