Hydrochloric Acid → N-(4-Acetyl-2-methylphenyl)methanesulfonamide

HRID 1438417Notes

Reaction equation

HRID 1438417 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[Cl-].[Al+3].[Cl-].[Cl-].[C:17](Cl)(=[O:19])[CH3:18].Cl>ClCCl.C1(C)C=CC=CC=1>[C:17]([C:6]1[CH:5]=[CH:4][C:3]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:2]([CH3:1])[CH:7]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 5065377HCID 5065377, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-methylphenyl)methanesulfonamide (1.84 g, 10 mmol) in dichloromethane (2 mL) was added aluminum chloride (3.3 g, 25 mmol) carefully at 0° C. Then acetyl chloride (1.07 ml, 15 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 0.5 hours, the reaction was monitored by using TLC and 1H-NMR, and after completion of the reaction, the reaction mixture was diluted with toluene and poured into 2N HCl aqueous solution with stirring at 0° C. The precipitate solid was filtered, washed with H2O, and dried to give a mixture of the title compound and by-product (N-acetylated product) (2.31g, ratio; title compound: by-product=81:19 (ratio was determined by 1H-NMR)) as a flesh color powder.

Workup

  1. custom1H-NMR, and after completion of the reaction
  2. stirringwith stirring at 0° C
  3. filtrationThe precipitate solid was filtered
  4. washwashed with H2O
  5. customdried
  6. customto give

Sources & evidence

ORD record
ord-b4b2570970324df2a5d5df966b07bbab
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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