Water → N-[2-(2-methoxyphenyl)ethyl]methanesulfonamide

HRID 480297

Reaction equation

HRID 480297 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[CH2:11][CH2:12][NH2:13].[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C(Cl)Cl>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[CH2:11][CH2:12][NH:13][S:19]([CH3:18])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 748962-Methoxyphenethylamine

Product 1

HCID 6465664N-[2-(2-methoxyphenyl)ethyl]methanesulfonamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Pyridine (12.0 mL, 150 mmol) was added to a solution of 2-methoxyphenethylamine (15.1 g, 100 mmol) in CH2Cl2 (100 mL). The reaction was cooled to 0° C. and methanesulfonyl chloride (12.6 g, 110 mmol) was added. The reaction was stirred at 0° C. for 0.5 h and at room temperature for 2 h. Water was added and the aqueous layer was extracted with CH2Cl2 (2×). The organic solution was washed water (1×) and brine (1×), dried over MgSO4, filtered and concentrated to afford N-[2-(2-methoxy-phenyl)-ethyl]-methanesulfonamide (18.5 g).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  2. washThe organic solution was washed water (1×) and brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b56e16f5e593495a98884fe4aa358fc5
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Linked notes

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