Pyridine → N-(3-{[2-(acetylamino)-7-nitro-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide

HRID 1097508Notes

Reaction equation

HRID 1097508 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH:18]=[CH:19][CH:20]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[C:34](Cl)(=[O:36])[CH3:35]>O1CCCC1.C(OCC)(=O)C>[C:34]([NH:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:24])[F:25])[CH:18]=[CH:19][CH:20]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86644700N-{3-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 86644701N-(3-{[2-(acetylamino)-7-nitro-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (1.2 g, 3.0 mmol) in tetrahydrofuran (20 mL) were added pyridine (2.4 mL, 30 mmol) and acetyl chloride (340 μL, 4.8 mmol), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was diluted with ethyl acetate (200 mL), washed successively with water (100 mL), 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=50/50→100/0), and the obtained solution was concentrated under reduced pressure to give the title compound as a yellow powder. This was directly used for the next reaction without further purification.

Workup

  1. washwashed successively with water (100 mL), 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=50/50→100/0)
  6. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f59a52baebf54277a10c663f1bf7e17c
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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