Water → HCID 86655396, compound

HRID 2190458Notes

Reaction equation

HRID 2190458 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[C:31](Cl)(=[O:33])[CH3:32].O>O1CCCC1.C(OCC)(=O)C>[C:31]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 86655395N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 86655396HCID 86655396, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (10.0 g, 28.3 mmol) and pyridine (3.36 g, 42.5 mmol) in tetrahydrofuran (150 mL) was added acetyl chloride (2.44 g, 31.1 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture were added water (300 mL) and ethyl acetate (500 mL), and the mixture was stirred for 30 min and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was triturated with ethyl acetate/diisopropyl ether to give the title compound (10.6 g, 95%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was triturated with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-4074b34739f846db8f00cc393d555ef3
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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