Dimethyl Sulfate → HCID 19360266, compound

HRID 1728620Notes

Reaction equation

HRID 1728620 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(OC)(O[CH3:24])(=O)=O>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]([CH3:24])[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 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 19360159HCID 19360159, compound

Product 1

HCID 19360266HCID 19360266, compoundYield 167.6%

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 anion formation was completed dimethyl sulfate (1.6 g, 12.7 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 3 g of a brown oil. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography yielded 1.7 g of an amber oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 1.4 g of yellow crystals, mp 280°-281° C.

Workup

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

Sources & evidence

ORD record
ord-00517723c88344c1b38ba5ff75a2ac4c
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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