Triethylamine → 5-Chloro-N-[2-(dimethylamino)ethyl]-2-thiophenesulfonamide

HRID 268959Notes

Reaction equation

HRID 268959 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[Cl:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][CH:9]=1.C(N(CC)CC)C>C1COCC1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][S:13]([C:11]1[S:12][C:8]([Cl:7])=[CH:9][CH:10]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 27339255-Chlorothiophene-2-sulfonyl chloride

Product 1

HCID 50132195-Chloro-N-[2-(dimethylamino)ethyl]-2-thiophenesulfonamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-dimethylamino-ethylamine (1.61 g, 13.8 mmol) in THF (20 mL) was added at 0° C. (ice water bath) commercially available 5-chloro-thiophene-2-sulfonyl chloride (1.0 g, 4.61 mmol) and triethylamine (0.71 mL, 5.07 mmol). The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by flash chromatography (ethyl acetate/MeOH) to yield the title compound (1.23 g, 99%) as a light yellow oil. MS (ISP) 269.0 [(M+H)+].

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography (ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-3959876fef494f49846b1a342fd2e74d
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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