Water → 5-bromo-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide

HRID 1484920Notes

Reaction equation

HRID 1484920 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][NH2:15].O>O1CCOCC1>[Br:1][C:2]1[S:6][C:5]([S:7]([NH:15][CH2:14][CH2:13][N:12]([CH3:16])[CH3:11])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 87167995-bromo-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromothiophene-2-sulfonyl chloride (2.0 g, 7.6 mmol, 1.0 eq) and N,N-dimethyl ethane-1,2-diamine (1.0 g, 11.5 mmol, 1.5 eq) in dioxane (20 mL) was stirred at room temperature for 2 h. Water was added and the reaction was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography to afford 5-bromo-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide (1.35 g, 94%). LC-MS (m/z)=313.0, 315.0 [M+H]+.

Workup

  1. extractionthe reaction was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f612321eff2047afb1bdc3617f8e3ed9
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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