1,4-Dioxane → HCID 26696954, compound

HRID 1591861Notes

Reaction equation

HRID 1591861 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].O1CCOCC1.[Cl:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C(OCC)(=O)C>[Cl:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[C:21]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:22]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 677684-Fluoro-3-nitroanilineHCID 27365462-Chloro-4-fluorobenzoyl chloride

Product 1

HCID 26696954HCID 26696954, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-fluoro-3-nitroaniline (1.0 g, 6.4 mmol) with dioxane (20 mL). Treat mixture with 2-chloro-4-fluorobenzoyl chloride (1.6 g, 8.3 mmol). Stir the reaction overnight at room temperature. Transfer the reaction mixture into ethyl acetate (220 mL), then wash successively with aqueous HCl (1N, 50 mL), aqueous NaOH (1N, 50 mL), saturated aqueous NaCl (50 mL). Dry the organic layer over anhydrous sodium sulfate, then evaporate the solvent under reduced pressure. Further purify the residue by chromatography on silica gel, using a gradient of 10–30% ethyl acetate in hexanes to obtain the title intermediate (1.7 g, 85% yield): mass spectrum (ion spray): m/z=313.0 (M+1).

Workup

  1. customthe reaction overnight at room temperature
  2. washwash successively with aqueous HCl (1N, 50 mL), aqueous NaOH (1N, 50 mL), saturated aqueous NaCl (50 mL)
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. customevaporate the solvent under reduced pressure
  5. customFurther purify the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-9087b76bc4534c9da81985fc6ee60bb2
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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