P-Anisidine → HCID 2829315, compound

HRID 1787995Notes

Reaction equation

HRID 1787995 reaction equation
COC1C=CC(N)=CC=1.C(N(CC)CC)C.[N+](C1C=C(S(Cl)(=O)=O)C=CC=1)([O-])=O.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([N:38](C2C=CC(OC)=CC=2)[S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([N+:48]([O-:50])=[O:49])[CH:43]=2)(=[O:41])=[O:40])=[CH:34][CH:33]=1>ClCCl>[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([N+:48]([O-:50])=[O:49])[CH:43]=2)(=[O:41])=[O:40])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 8471Triethylamine2×HCID 84763-Nitrobenzenesulfonyl chloride2×HCID 57434738HCID 57434738, compound

Product 1

HCID 2829315HCID 2829315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 250 mL round bottom flask was equipped with a magnetic stirrer. The flask was charged with p-anisidine (13.0 mmol) followed by dichloromethane (50 mL). Triethylamine (25.9 mmol) was added followed by 3-nitrobenzenesulfonyl chloride (16.2 mmol). Additional dichloromethane (75 mL) was added for solubility. The reaction was allowed to stir overnight. After 18 hours, TLC (dichloromethane/silica) indicated that the reaction was not complete. One additional equivalent of 3-nitrobenzenesulfonyl chloride (13.0 mmol), and two equivalents of triethylamine (25.9 mmol) were added to the reaction. After 10 minutes, TLC indicated that two products had formed and all starting anisidine was consumed. The reaction was washed with 2N HCl (100 mL), dried (Na2SO4), filtered, and the solvent removed under diminished pressure. The residue was dissolved in dichloromethane (20 mL) and loaded onto a 600 mL sintered glass funnel charged with silica gel (400 g). The silica plug was eluted with dichloromethane (100 mL fractions) until the first product eluted from the filter column (TLC, dichloromethane/silica). The solvent system was changed to 9:1 dichloromethane/ethyl acetate and fractions were taken (100 mL) until the second product eluted from the filter column. The solvent from both samples was removed under reduced pressure to yield a mixture of the undesired N,N-bis-(4-methoxyphenyl)-3-nitrobenzenesulfonamide and the desired product.

Workup

  1. customA 250 mL round bottom flask was equipped with a magnetic stirrer
  2. waitAfter 18 hours
  3. waitAfter 10 minutes
  4. customhad formed
  5. customall starting anisidine was consumed
  6. washThe reaction was washed with 2N HCl (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent removed under diminished pressure
  10. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  11. customloaded onto a 600 mL sintered glass funnel
  12. additioncharged with silica gel (400 g)
  13. washThe silica plug was eluted with dichloromethane (100 mL fractions) until the first product
  14. washeluted from the filter column (TLC, dichloromethane/silica)
  15. washeluted from the filter column
  16. customThe solvent from both samples was removed under reduced pressure
  17. customto yield

Sources & evidence

ORD record
ord-50ee35fe8d024b7b9ec747792df57b47
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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