Dimethylformamide → HCID 67485762, compound

HRID 1880596Notes

Reaction equation

HRID 1880596 reaction equation
CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15](F)[CH:14]=1.[OH:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1>C(OCC)(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([CH:14]=1)[O:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 10340Sodium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 67485762HCID 67485762, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A DMF (4 mL) solution containing Na2CO3 (60 mg, 0.57 mmol), 4-chloro-2-fluoro-1-nitrobenzene (100 mg, 0.57 mmol) and methyl 4-hydroxybenzoate (87 mg, 0.57 mmol) was stirred at room temperature for 8 hours. HPLC analysis indicated ca. 85% product. The reaction solution was stirred for an additional 2 hours at 40° C. The solution was then diluted with ethyl acetate and washed with 1N NaOH. The organic phase was washed with water (3×), brine and dried over Na2SO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 8.11 (d, J=8.1 Hz, 2H); 8.01 (d, J=8.2 Hz, 1H); 7.31-7.27 (m, 1H); 7.11-7.07 (m, 3H); 3.95 (s, 3H). LCMS1 3.66 min. (M+H)=308.

Workup

  1. stirringThe reaction solution was stirred for an additional 2 hours at 40° C
  2. washwashed with 1N NaOH
  3. washThe organic phase was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-34919437f296470d9375a144ad46fe8b
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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