Hydrochloric Acid → Thieno(2,3-c)pyridine

HRID 507675Notes

Reaction equation

HRID 507675 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)S(C1C=CC(C)=CC=1)(=O)=O.Cl.[OH-].[Na+]>O1CCOCC1.O>[S:18]1[C:17]2=[CH:16][N:5]=[CH:4][CH:3]=[C:21]2[CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 334477N-(2,2-dimethoxyethyl)-4-methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide

Product 1

HCID 9224Thieno(2,3-c)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2,2-Dimethoxyethyl)-4-methyl-N-(thiophen-2-ylmethyl)benzenesulfonamide (7 g, 19 mmol) was dissolved in dioxane (10 mL) and treated with concentrated HCl (10 mL). The mixture for heated to reflux for 12 h. The mixture was allowed to cool down to room temperature, diluted with water (20 mL) and brought to pH 7 with 2 N sodium hydroxide. The mixture was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 10 to 60% ethyl acetate in hexanes to obtain a tan solid. Yield=1 g. MS (M+H)+ 136.

Workup

  1. temperatureThe mixture for heated
  2. temperatureto reflux for 12 h
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated
  7. custompurified by flash chromatography
  8. customto obtain a tan solid

Sources & evidence

ORD record
ord-50bb974d256a4ddd956df49c78c11e41
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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