Phenethylamine → Methanesulfonamide, N-(2-phenylethyl)-

HRID 392454Notes

Reaction equation

HRID 392454 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 118569Methanesulfonamide, N-(2-phenylethyl)-Yield 106.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10° C. solution of phenethylamine (12.1 g, 0.100 mol) and triethylamine (11.1 g, 0.110 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (12.6 g, 0.110 mol) dropwise over 10 min. The solution was stirred at room temperature for 1.5 h and was then washed with 1 N HCl (5×20 mL). The organic phase was directly concentrated to provide the intermediate title compound, N-(methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. 1H NMR (300 MHz) 7.32 (m, 2H), 7.23 (m, 3H), 4.30 (br s, 1H), 3.40 (t, 2H, J=3.9), 2.88 (t, 2H, J=4.2), 2.81 (s, 3H).

Workup

  1. washwas then washed with 1 N HCl (5×20 mL)
  2. concentrationThe organic phase was directly concentrated

Sources & evidence

ORD record
ord-a1b43f693aff48dc9d6cd293b2175760
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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