Triethylamine → HCID 67258204, compound

HRID 2371042Notes

Reaction equation

HRID 2371042 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7](O)[CH2:8][N+:9]([O-:11])=[O:10].CCN(CC)CC.CS(Cl)(=O)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1/[CH:7]=[CH:8]/[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67256195HCID 67256195, compound

Product 1

HCID 67258204HCID 67258204, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-bromothiophen-3-yl)-2-nitroethanol (3 g, 12.0 mmol), DMAP (146 mg, 1.2 mmol) and Et3N (2.4 g, 24.0 mmol) in DCM (30 mL) was added MsCl (2.4 g, 24.0 mmol) dropwise. The resulting mixture was then refluxed for 3 h. After cooling, the reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (2.5 g, 88%).

Workup

  1. temperatureThe resulting mixture was then refluxed for 3 h
  2. temperatureAfter cooling
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8f2f7dadcfb54f70a3ac5351c3838360
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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