Triethylamine → HCID 936105, compound

HRID 268972Notes

Reaction equation

HRID 268972 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Br:9][C:10]1[S:14][C:13]([S:15](Cl)(=[O:17])=[O:16])=[CH:12][CH:11]=1.C(N(CC)CC)C>C1COCC1>[N:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:1][S:15]([C:13]2[S:14][C:10]([Br:9])=[CH:11][CH:12]=2)(=[O:17])=[O:16])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 936105HCID 936105, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-aminomethyl-pyridine (1.24 g, 11.5 mmol) in THF (8 ml) was added at 0° C. (ice water bath) commercially available 5-bromo-thiophene-2-sulfonyl chloride (1.0 g, 3.82 mmol) dissolved in THF (8 ml) and triethylamine (0.59 ml, 4.21 mmol). The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by flash chromatography (dichloromethane/methanol) and crystallization from dichloromethane/hexane to yield the title compound (1.21 g, 95%) as a white solid. MS (ISN) 330.8 [(M−H)−], mp 159° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography (dichloromethane/methanol) and crystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-04240e16e90b434b94ff36fca417a124
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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