2-Methoxyethylamine → 2,4-dichloro-N-(2-methoxyethyl)benzenesulfonamide

HRID 1792768Notes

Reaction equation

HRID 1792768 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][O:14][CH2:15][CH2:16][NH2:17]>C(O)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9](=[O:11])(=[O:10])[NH:17][CH2:16][CH2:15][O:14][CH3:13]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-

Product 1

HCID 159439402,4-dichloro-N-(2-methoxyethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2,4-Dichlorobenzenesulphonyl chloride (500 mg 2.1 mmol) and 2-methoxyethylamine (230 mg, 3.1 mmol) in n-butanol (10 ml) was heated at reflux for one hour. The volatiles were removed by evaporation and residue purified by chromatography eluting with hexane/ethyl acetate (50:50) to give the title compound. NMR: 3.04 (t, 2H), 3.08 (s, 3H), 3.22 (t, 2H), 7.60 (dd, 1H), 7.82 (d, 1H), 7.92 (d, 1H), 8.0 (s, 1H); m/z: 282 [M−H]−.

Workup

  1. temperatureat reflux for one hour
  2. customThe volatiles were removed by evaporation and residue
  3. custompurified by chromatography
  4. washeluting with hexane/ethyl acetate (50:50)

Sources & evidence

ORD record
ord-b4541496d65843e8ba39b6459bbb8b7e
Source dataset
uspto-grants-2006_07
Patent number
US07078410B2

Reaction notes

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