Diethanolamine → 5-Bromo-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amide

HRID 1293642Notes

Reaction equation

HRID 1293642 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[Br:8][C:9]1[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][CH:10]=1.C(N(CC)CC)C>C1COCC1>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[S:14]([C:12]1[S:13][C:9]([Br:8])=[CH:10][CH:11]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 612345545-Bromo-thiophene-2-sulfonic acid bis-(2-hydroxy-ethyl)-amideYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of diethanolamine (1.45 g, 13.8 mmol) in THF (20 ml) was added at 0° C. (ice water bath) commercially available 5-bromo-thiophene-2-sulfonyl chloride (1.0 g, 3.82 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/heptane) to yield the title compound (0.98 g, 77%) as a white solid. MS (ISP) 330.0 [(M+H)+], mp 70° C.

Workup

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

Sources & evidence

ORD record
ord-0f0bcbfb816c40999fe5c8cd69f54f5f
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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