P-Anisidine → N-(4-methoxyphenyl)-2-nitrobenzenesulfonamide

HRID 1787993Notes

Reaction equation

HRID 1787993 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27])([O-:19])=[O:18].S(Cl)(Cl)(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N+:17]([O-:19])=[O:18])(=[O:27])=[O:28])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 24648Sulfuryl chloride2×

Product 1

HCID 836015N-(4-methoxyphenyl)-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 250 mL round bottom flask was equipped with a magnetic stirrer, charged with p-anisidine (13.0 mmol), followed by dichloromethane (75 mL). The flask was then placed in an ice bath to chill the contents. Triethylamine was added and an addition funnel was installed. The addition funnel was charged with 2-nitrobenzenesulfonyl chloride (32.4 mmol) in dichloromethane (75 mL). The sulfonyl chloride was added dropwise very slowly and the reaction monitored by TLC (dichloromethane/silica) several times during the addition. The reaction was complete after addition of 50 mL (21.6 mmol) of the sulfonyl chloride solution. The reaction solvent was removed at 0° C. and immediately loaded onto a 600 mL sintered glass funnel charged with silica gel (400 g), eluted with dichloromethane collecting 100 mL fractions. Fractions containing the desired product were combined and evaporated under diminished pressure to yield the title compound as a yellow powder in excellent yield. 3.67 g, (92%). 1H-NMR (CDCl3): δ 3.20 (s, 3H); 6.78-6.79 (d, 2H, J=8.9 Hz); 7.07-7.10 (d, 3H, J=8.9 Hz); 7.53-7.58 (t, 1H, J=7.7 Hz); 7.66-7.71 (t, 1H, J=7.8 Hz); 7.73-7.76 (d, 1H, J=7.8 Hz); 7.84-7.87 (d, 1H, J=7.9 Hz).

Workup

  1. customA 250 mL round bottom flask was equipped with a magnetic stirrer
  2. customThe flask was then placed in an ice bath
  3. temperatureto chill the contents
  4. customan addition funnel was installed
  5. customThe reaction solvent was removed at 0° C.
  6. customimmediately loaded onto a 600 mL sintered glass funnel
  7. additioncharged with silica gel (400 g)
  8. washeluted with dichloromethane collecting 100 mL fractions
  9. additionFractions containing the desired product
  10. customevaporated under diminished pressure

Sources & evidence

ORD record
ord-e3ed68e1e6f14730921c2f5e65b92082
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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