Ethylamine → N-Ethyl-4-methoxybenzenesulfonamide

HRID 2077510Notes

Reaction equation

HRID 2077510 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:13]([NH2:15])[CH3:14]>C(Cl)Cl>[CH2:13]([NH:15][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH3:14]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 74014-Methoxybenzenesulfonyl chloride

Product 1

HCID 4453230N-Ethyl-4-methoxybenzenesulfonamideYield 112%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzene-1-sulfonyl chloride (619.5 mg, 2.999 mmol) was dissolved in DCM (10 mL) and ethylamine (4.6 mL, 2.0 M in THF, 9.2 mmol) was added, and the reaction flask was put in a water bath and stirred under nitrogen. After stirring at RT over the weekend, the suspension was filtered, and the solid was washed with DCM. The filtrate was concentrated and dried under high vacuum to provide N-ethyl-4-methoxybenzenesulfonamide (723 mg, 89% yield). MS (ESI pos. ion) m/z: 216 (MH+). Calculated exact mass for C9H13NO3S: 215.

Workup

  1. customthe reaction flask was put in a water bath
  2. stirringAfter stirring at RT over the weekend
  3. filtrationthe suspension was filtered
  4. washthe solid was washed with DCM
  5. concentrationThe filtrate was concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-5cbd9edec7f444d98af3a89e42fafd73
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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