Hydrochloric Acid → 4-Methyl-N-(2,4,6-trimethylphenyl)benzenesulfonamide

HRID 1823191Notes

Reaction equation

HRID 1823191 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([NH:4][C:3]2[C:5]([CH3:10])=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=2[CH3:1])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69132,4,6-TrimethylanilineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 9250164-Methyl-N-(2,4,6-trimethylphenyl)benzenesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A 250-mL round-bottomed flask was charged with 2,4,6-trimethylaniline (mesidine, 11.88 mL, 84.62 mmol) and 50 mL of pyridine. To this mixture, a solution of p-toluenesulfonyl chloride (16.13 g, 84.62 mmol) in pyridine (50 mL) was added, and the reaction mixture was stirred at room temperature for 17 h. The reaction mixture was poured into 800 mL of acidic ice water containing 125 ml of 37% HCl. The mixture was cooled to 0° C. for 3 h, and a yellow solid precipitated. The yellow solid was collected by filtration and dissolved in 18 L of 5% NaOH. To this solution, 1850 mL of 37% HCl was added until the mixture reached a pH of 5. The resulting white precipitate was collected and washed with 800 mL of water and then dried in vacuo to give N-(p-toluenesulfonyl)-2,4,6-trimethylaniline (N-(p-toluenesulfonyl)mesidine) (21.73 g, 89%). 1H NMR (300 MHz, CDCl3): δ7.6 (d, 2H), 7.2 (d, 2H), 6.8 (s, 2H), 5.9 (s, 1H), 2.4 (s, 3H), 2.3 (s, 3H) 2.0 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to 0° C. for 3 h
  2. customa yellow solid precipitated
  3. filtrationThe yellow solid was collected by filtration
  4. dissolutiondissolved in 18 L of 5% NaOH
  5. additionTo this solution, 1850 mL of 37% HCl was added until the mixture
  6. customThe resulting white precipitate was collected
  7. washwashed with 800 mL of water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b97bd16006824fc9af5819fa1e458e15
Source dataset
uspto-grants-2006_05
Patent number
US07037990B2

Reaction notes

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