Pyridine → N-(4-methoxy-2-methylphenyl)methanesulfonamide

HRID 1244038Notes

Reaction equation

HRID 1244038 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[CH:4]=1.N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][S:18]([CH3:17])(=[O:20])=[O:19])=[C:5]([CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 76102-Methyl-4-methoxyanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 15851883N-(4-methoxy-2-methylphenyl)methanesulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.85 gm (50 mmol) 4-methoxy-2-methylaniline in 70 ml of methylene chloride was introduced 8.5 gm (ml; mmol) pyridine followed by dropwise addition of 6.87 gm (60 mmol) methanesulfonylchloride. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was washed with 1N HCl and then with saturated aqueous brine. The organics were dried with sodium sulfate and then evaporated in vacuo. The residue was triturated in diethyl ether to afford 7.5 gm (79%) of a light purple solid. Mass spectrum APCI (m/z) 216 (p+1).

Workup

  1. washThe reaction mixture was washed with 1N HCl
  2. dry with materialThe organics were dried with sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-b12c457274b54cfcb76e4f6b8c174444
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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