Methane → HCID 10755187, compound

HRID 1166400Notes

Reaction equation

HRID 1166400 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]([CH2:18][C:19](=O)[CH3:20])[C:15]([CH3:17])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:20][C:19]1[N:13]([S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[C:15]([CH3:17])=[CH:14][CH:18]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 227844-Nitrobenzenesulfonamide

Product 1

HCID 10755187HCID 10755187, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitrobenzenesulfonamide (30.3 g, 0.15 mol), acetonylacetone (34.2 g, 0.30 mol) and 4-toluenesulfonic acid (3.0 g, catalyst) in 200 mL of toluene was heated at reflux under nitrogen using a Dean-Stark trap for 18 hours. The reaction was cooled and filtered through silica gel (700 g), eluting with mixtures of ethyl acetate and hexane. Removal of solvent in vacuo gave a crude brown solid. The crude product in ethyl acetate was treated with activated charcoal, and recrystallized from ethyl acetate and hexane to afford 4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]nitrobenzene (32.5 g, 77%) as a light yellow solid: mp (DSC): 101-103° C. Anal. Calc'd. for C12H12N2O4S: C, 51.42; H, 4.32; N, 9.99; S, 11.44. Found: C, 51.62; H, 4.18; N, 9.96; S, 11.31.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen using a Dean-Stark trap for 18 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered through silica gel (700 g)
  5. washeluting with mixtures of ethyl acetate and hexane
  6. customRemoval of solvent in vacuo
  7. customgave a crude brown solid
  8. customrecrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-2ba3f1f5a66944d0b2057309a9a232e6
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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