Tetrahydrofuran → HCID 86644689, compound

HRID 455192Notes

Reaction equation

HRID 455192 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[C:18]#[N:19])=[CH:6][C:5]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:4]([F:27])[CH:3]=1.O1CCCC1>C(O)(=O)C>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[C:2]([Cl:1])=[CH:3][C:4]([F:27])=[C:5]([NH:20][C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])[CH:6]=2)=[C:10]([C:18]#[N:19])[CH:11]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86644688N-[4-chloro-5-(2-cyano-4-nitrophenoxy)-2-fluorophenyl]-2,2,2-trifluoroacetamide

Product 1

HCID 86644689HCID 86644689, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-[4-chloro-5-(2-cyano-4-nitrophenoxy)-2-fluorophenyl]-2,2,2-trifluoroacetamide (16.0 g, 39.6 mmol) in acetic acid (850 ml)/tetrahydrofuran (500 mL) was added reduced iron (11.1 g, 198 mmol), and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off through a pad of celite, and washed with acetic acid. The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (900 mL)/tetrahydrofuran (100 mL), washed successively with saturated aqueous sodium hydrogen carbonate solution (500 mL) and saturated brine (500 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 silica gel column chromatography (ethyl acetate/n-hexane=10/90→50/50), and the obtained solution was concentrated under reduced pressure to give the title compound (12.2 g, 82%) as a white powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off through a pad of celite
  3. washwashed with acetic acid
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with ethyl acetate (900 mL)/tetrahydrofuran (100 mL)
  6. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (500 mL) and saturated brine (500 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationInsoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=10/90→50/50)
  11. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-733dc95ba2db4c3eae1b2adff200595b
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

Loading…