Sulfuric Acid → HCID 86737989, compound

HRID 1577484Notes

Reaction equation

HRID 1577484 reaction equation
S(=O)(=O)(O)O.[CH2:6]([CH:8]([NH:11][C:12]1[C:13]([N+:27]([O-:29])=[O:28])=[CH:14][C:15]([CH2:24][CH:25]=[O:26])=[C:16]([CH:21]([CH3:23])[CH3:22])[C:17]=1[N+:18]([O-:20])=[O:19])[CH2:9][CH3:10])[CH3:7].[Mn]([O-])(=O)(=O)=[O:31].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.O>[CH2:6]([CH:8]([NH:11][C:12]1[C:13]([N+:27]([O-:29])=[O:28])=[CH:14][C:15]([CH2:24][C:25]([OH:31])=[O:26])=[C:16]([CH:21]([CH3:22])[CH3:23])[C:17]=1[N+:18]([O-:20])=[O:19])[CH2:9][CH3:10])[CH3:7]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24477Sodium ThiosulfateHCID 516875Potassium Permanganate2×HCID 86737990HCID 86737990, compound

Product 1

HCID 86737989HCID 86737989, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
12 °C

Procedure

A mixture of concentrated sulfuric acid (4.25 g) and water (17.3 g) is cooled to about 12° C., and a solution of {5-[(1-ethylpropyl)amino]-4,6-dinitro-o-cumenyl}acetaldehyde (6.5 g; 0.0192 mol) in methylene chloride (40 ml) is added slowly while the temperature of the mixture is maintained at about 12° C. Next, potassium permanganate (3.0 g; 0.0192 mol) is added to small portions. After stirring overnight at room temperature, tlc indicates the presence of some starting material. The mixture is cooled to 15° C., and a second portion of potassium permanganate (3.0 g; 0.0192 mol) added. When tlc indicates the absence of starting material, sodium thiosulfate is added until a clear red solution is obtained. Methylene chloride is added and the layers are separated. The methylene chloride layer is washed, dried over magnesium sulfate, and evaporated to leave a red oil (6.6 g; 97%) which slowly solidifies to a yellow solid. This solid is purified by column chromatography using 90/10 toluene/ethyl acetate to elute the product, melting point 116°-118° C. An analytical sample, recrystallized from pentane, melts at 117.5°-118.5° C.

Workup

  1. temperatureis maintained at about 12° C
  2. temperatureThe mixture is cooled to 15° C.
  3. additionis added until a clear red solution
  4. customis obtained
  5. customthe layers are separated
  6. washThe methylene chloride layer is washed
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto leave a red oil (6.6 g; 97%) which
  10. customThis solid is purified by column chromatography
  11. washto elute the product, melting point 116°-118° C
  12. customAn analytical sample, recrystallized from pentane, melts at 117.5°-118.5° C.

Sources & evidence

ORD record
ord-75b6dcd289394b7ebd3077507301ab0e
Source dataset
uspto-grants-1981_09
Patent number
US04288385

Reaction notes

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