1-Bromopropane → HCID 19360190, compound

HRID 1728622Notes

Reaction equation

HRID 1728622 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][CH3:23]>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]([CH2:21][CH2:22][CH3:23])[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 78401-BromopropaneHCID 24758Sodium hydrideHCID 19360159HCID 19360159, compound

Product 1

HCID 19360190HCID 19360190, compoundYield 128.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-3-(4-pyridinylamino)benzo[b]thiophene (4.2 g, 16.1 mmol) was added portionwise as a powder to an ice-cooled suspension of sodium hydride (60% oil dispersion, 0.8 g, 20 mmol, washed with heptane) in 25 mL of dimethylformamide. After the anion formation was completed, 1-bromopropane (2 g, 16.3 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 a brown oil. Elution through silica with 10% methanol in ethyl acetate via flash column chromatography yielded 3.5 g of an amber oil. Conversion to the hydrochloride salt in 10% methanol in ether afforded 3.7 g of a pale yellow powder, mp 276°-277° C.

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 to a brown oil
  8. washElution through silica with 10% methanol in ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-381c8f5416bb4174a2ac243ab9034f14
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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