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

HRID 1611079Notes

Reaction equation

HRID 1611079 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 1N 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.

Workup

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

Sources & evidence

ORD record
ord-f41c03bc4a954803a615241c2fef61de
Source dataset
uspto-grants-2006_01
Patent number
US06984756B2

Reaction notes

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