Sodium hydride → HCID 19360194, compound

HRID 376882Notes

Reaction equation

HRID 376882 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+].Cl[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][C:26]=1[O:34][CH3:35]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][C:26]=3[O:34][CH3:35])=[CH:8][S:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 19360159HCID 19360159, compound

Product 1

HCID 19360194HCID 19360194, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (4 g, 15 mmol) was added portionwise as a powder to a suspension of sodium hydride (60% oil dispersion, 0.7 g, 18 mmol, washed with heptane) in 50 mL of dimethylformamide. After the anion formation was completed, 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4 g, 16 mmol) was added. The reaction mixture was stirred two hours at 45° C., and then was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution, and then was dried (anhydrous magnesium sulfate), filtered and concentrated to 8 g of a dark oil. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography afforded 4.1 g of a brown oil. Elution of this oil three times through silica with ethyl acetate via flash column chromatography afforded 3.0 g of a waxy solid. Recrystallization from acetonitrile afforded 2.1 g of white crystals, mp 148-149° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and saturated sodium chloride solution
  4. dry with materialwas dried (anhydrous magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated to 8 g of a dark oil
  7. washElution through silica with 10% methanol in ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-63751ca083444f0cb3dc58a86e05484e
Source dataset
uspto-grants-2000_02
Patent number
US06022880

Reaction notes

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