Dimethyl Sulfoxide → [2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester

HRID 640957Notes

Reaction equation

HRID 640957 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[CH:13][C:12]=1[N+:28]([O-:30])=[O:29])C(OCC)=O)[CH3:2].CS(C)=O.O>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[CH:13][C:12]=1[N+:28]([O-:30])=[O:29])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 59256487Diethyl 2-(2-nitro-4-(3-nitrobenzoyl)phenyl)malonate

Product 1

HCID 86610408[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A 2 L, 3-necked round bottomed flask equipped with a heating mantle, condenser, overhead stirrer, thermocouple, and N2(g) inlet was charged with 2-[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-malonic acid diethyl ester (105 g, 0.24 mol), DMSO (1 L) and H2O (87 mL). The reaction was heated at 110° C. for 11 h. Thin layer chromatographic analysis (Hexanes/ethylacetate 6:4) indicated completion of reaction. The reaction mixture was cooled to room temperature and was diluted with ethyl acetate (4 L). The organic layer was washed with brine (3×4 L), dried over Na2SO4 and concentrated. Methyl t-butyl ether (1 L) was added to the solids and stirred. The product was filtered and washed with Methyl t-butyl ether (2×250 mL). The solids collected were dried in the vacuum oven at 45° C. for 24 hours to yield 89% of pure [2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester (77 g, 0.21 mol).

Workup

  1. customA 2 L, 3-necked round bottomed flask equipped with a heating mantle, condenser, overhead stirrer
  2. customcompletion of reaction
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washThe organic layer was washed with brine (3×4 L)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. additionMethyl t-butyl ether (1 L) was added to the solids
  8. filtrationThe product was filtered
  9. washwashed with Methyl t-butyl ether (2×250 mL)
  10. customThe solids collected
  11. customwere dried in the vacuum oven at 45° C. for 24 hours

Sources & evidence

ORD record
ord-2eb4e2b315244786ae4a733e7cf96441
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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