Phenethylamine → N-Phenethylbenzenesulfonamide

HRID 2407627Notes

Reaction equation

HRID 2407627 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:8]([NH:9][S:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:25])=[O:24])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 254130N-PhenethylbenzenesulfonamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-phenylethylamine (2 g, 16.5 mmol) in 105 ml DMF at room temperature was added Et3N (2.75 ml, 19.8 mmol). This mixture was stirred for 5 min, and then benzenesulfonyl chloride (2.3 ml, 18.1 mmol) was added at this temperature. The reaction was stirred for 2.5 h, and then, the mixture was evaporated to dryness and the crude was chromatographically purified over SiO2 using Hexane/AcOEt 60/40 as the eluant, yielding 3.12 g (72%) of the desired product.

Workup

  1. stirringThe reaction was stirred for 2.5 h
  2. customthe mixture was evaporated to dryness
  3. customthe crude was chromatographically purified over SiO2

Sources & evidence

ORD record
ord-f8c2a7f049a9471082f22abc058bd5a8
Source dataset
uspto-grants-2014_08
Patent number
US08809584B2

Reaction notes

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