Butyl bromide → HCID 19014473, compound

HRID 1728624Notes

Reaction equation

HRID 1728624 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+].Br[CH2:21][CH2:22][CH2:23][CH3:24]>CN(C)C=O>[ClH:1].[CH2:21]([N:10]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[C:9]1[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][C:6]=2[S:7][CH:8]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 19360159HCID 19360159, compound

Product 1

HCID 19014473HCID 19014473, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (5 g, 19 mmol) was added portionwise as a powder to a suspension of sodium hydride (60% oil dispersion, 0.8 g, 20 mmol, washed with heptane) in 50 mL of dimethylformamide. After the anion formation was completed, 1-bromobutane (2.8 g, 20 mmol) was added. After stirring one hour, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution, and dried (anhydrous magnesium sulfate), filtered and concentrated. Elution of the residue through silica with 5% methanol in ethyl acetate via flash column chromatography afforded 3.7 g of an oil. Elution through alumina with ether via column chromatography afforded 3.3 g of an oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 3.2 g of white crystals, mp 259°-260° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and saturated sodium chloride solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washElution of the residue through silica with 5% methanol in ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-743320b8a69e4b4984638288ced31dea
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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