Methanesulfonyl chloride → N-[(4-Methoxyphenyl)Methyl]Methanesulfonamide

HRID 1962345Notes

Reaction equation

HRID 1962345 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][S:12]([CH3:11])(=[O:14])=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 754524-Methoxybenzylamine

Product 1

HCID 669028N-[(4-Methoxyphenyl)Methyl]MethanesulfonamideYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-methoxyphenyl)methanamine (1.317 g, 9.60 mmol) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (0.34 mL, 4.36 mmol) dropwise. The mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with 50 mL CH2Cl2 washed with 1N H3PO4, 10% NaCl, dried over anhydrous mgSO4, filtered and concentrated in vacuo to give the title compound as a white solid (0.84 g, 89%).

Workup

  1. washwashed with 1N H3PO4, 10% NaCl
  2. customdried over anhydrous mgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6156e2c65461435eaf0dfa4a24123951
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Reaction notes

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