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

HRID 2184394Notes

Reaction equation

HRID 2184394 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, (methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. 1H NMR (CDCl3, 300 MHz) δ7.32 (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-bdf136999f624cacb9a8ddf4ed3495fd
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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