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

HRID 558528Notes

Reaction equation

HRID 558528 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22]>C1COCC1>[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH:22][S:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 87167995-bromo-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of commercially available 5-bromo-thiophene-2-sulfonyl chloride (3.0 g, 11.5 mmol) in THF (22 ml) was added at room temperature triethylamine (1.76 ml, 12.6 mmol), the mixture was cooled (ice-water) and a solution of commercially available N,N-dimethyl-ethylenediamine (3.76 ml, 34.4 mmol) in THF (22 ml) was added drop wise. The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by column chromatography (dichloromethane/methanol/NH4OH 16:1:0.1) to yield the title compound (3.49 g, 97%) as a light yellow oil. MS (ISN) 310.9 [(M−H)−].

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography (dichloromethane/methanol/NH4OH 16:1:0.1)

Sources & evidence

ORD record
ord-f53eb9c9191e4e7f8400be77fa4da589
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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