2-Methoxyethylamine → 4-amino-N-(2-methoxyethyl)benzene-1-sulfonamide

HRID 1792766Notes

Reaction equation

HRID 1792766 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[S:6](F)(=[O:15])([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)=[O:7].C(N(CC)CC)C>C(O)CCC>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:15])=[O:7]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 668234-Aminobenzenesulfonyl fluoride

Product 1

HCID 167819184-amino-N-(2-methoxyethyl)benzene-1-sulfonamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-methoxyethylamine (859 mg, 11.4 mmol), sulphanilyl fluoride (1.0 g, 5.71 mmol), and triethylamine (1.72 g, 22.9 mmol) in n-butanol (15 ml) was heated at reflux for 18 hours. The mixture was allowed to cool and the volatiles were removed by evaporation. The residue was purified by chromatography eluting with ethyl acetate/hexane (50:50) increasing in polarity to (70:30) to give the title compound (860 mg, 65% yield). NMR: 2.78 (q, 2H), 3.15 (s, 3H), 3.25 (t, 2H), 5.87 (s, 2H), 6.58 (d, 2H), 7.10 (t, 1H), 7.40 (d, 2H); m/z: 231[MH]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureto cool
  4. customthe volatiles were removed by evaporation
  5. customThe residue was purified by chromatography
  6. washeluting with ethyl acetate/hexane (50:50)
  7. temperatureincreasing in polarity to (70:30)

Sources & evidence

ORD record
ord-1606dffd93e44b718532834e0f8c1c8d
Source dataset
uspto-grants-2006_07
Patent number
US07078410B2

Reaction notes

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