Triethylamine → 5-Bromo-N-[2-hydroxy-1-(hydroxymethyl)ethyl]-2-thiophenesulfonamide

HRID 268971Notes

Reaction equation

HRID 268971 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[Br: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>[OH:4][CH2:3][CH:2]([NH:1][S:13]([C:11]1[S:12][C:8]([Br:7])=[CH:9][CH:10]=1)(=[O:15])=[O:14])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68294SerinolHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 653146455-Bromo-N-[2-hydroxy-1-(hydroxymethyl)ethyl]-2-thiophenesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-amino-1,3-propanediol (1.26 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 (0.87 g, 72%) as a white solid. MS (ISN) 313.9 [(M−H)−], mp 80° C.

Workup

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

Sources & evidence

ORD record
ord-074f39445a7e4b8dbf927caca3c1204c
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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