Hydrochloric Acid → HCID 18965426, compound

HRID 2226568Notes

Reaction equation

HRID 2226568 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10](=[N:12]OC)[CH3:11])[S:7][C:6]=2[CH:15]=1.[BH4-].[Na+].B(F)(F)F.Cl>C(COC)OC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]([NH2:12])[CH3:11])[S:7][C:6]=2[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6356Boron trifluorideHCID 4311764Sodium borohydrideHCID 54118404HCID 54118404, compound

Product 1

HCID 18965426HCID 18965426, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Subsequently, 2.7 g of the crude 6-chloro-2-(1-methoxyiminoethyl)benzo[b]thiophene obtained was dissolved in 10 ml of dimethoxyethane, and the resultant solution was added dropwise at room temperature to a suspension of 0.85 g of sodium borohydride in 20 ml of dimethoxyethane. After agitating for 5 minutes at the same temperature, a solution containing 4.26 g of a boron trifluoride.diethyl ether complex in 5 ml of dimethoxyethane was then added dropwise at room temperature. After stirring for 30 minutes at the same temperature, the mixture was stirred for an additional 2 hours under reflux. The mixture was then allowed to cool to room temperature, after which 10% hydrochloric acid was added, adjusting the mixture to a pH of 3-4. The dimethoxyethane layer was concentrated and combined with the water layer, and the pH was raised to 7-8 using sodium carbonate. Extraction was then performed using dichloromethane, and the dichloromethane layer was then washed with water, dried over anhydrous magnesium sulfate, filtered through FLORISIL®, and concentrated to yield 0.35 g of the desired product, a transparent viscous fluid (refractive index nD20 =1.5973).

Workup

  1. stirringAfter stirring for 30 minutes at the same temperature
  2. stirringthe mixture was stirred for an additional 2 hours
  3. temperatureunder reflux
  4. concentrationThe dimethoxyethane layer was concentrated
  5. temperaturethe pH was raised to 7-8 using sodium carbonate
  6. extractionExtraction
  7. washthe dichloromethane layer was then washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered through FLORISIL®
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e01f7e00b16d4db4b9e285090c0419e0
Source dataset
uspto-grants-1994_09
Patent number
US05348976

Reaction notes

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