Diethyl Sulfate → HCID 19360254, compound

HRID 376880Notes

Reaction equation

HRID 376880 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([NH:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:8][S:7][C:6]=2[CH:17]=1.[H-].[Na+].S(OCC)(O[CH2:24][CH3:25])(=O)=O>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]([CH2:24][CH3:25])[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:8][S:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 19360159HCID 19360159, compound

Product 1

HCID 19360254HCID 19360254, compoundYield 267.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (3 g, 11.5 mmol) was added portionwise as a powder to an ice-cooled suspension of sodium hydride (60% oil dispersion, 0.7 g, 17.5 mmol, washed with heptane) in 25 mL of dimethylformamide. After the anion formation was completed, diethyl sulfate (1.8 g, 11.7 mmol) was added. After one hour the reaction mixture was poured into ice-water and extracted with ether. The organic extract was washed with water and saturated sodium chloride solution, and dried (anhydrous magnesium sulfate), filtered and concentrated to give 5 g of a brown oil. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography yielded 2.3 g of an amber oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 1.8 g of yellow crystals, mp 288-290°.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b8c8c474e97d4326bd7dd54f4398626a
Source dataset
uspto-grants-2000_02
Patent number
US06022880

Reaction notes

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