1-Bromohexane → HCID 59467510, compound

HRID 1715679Notes

Reaction equation

HRID 1715679 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=[CH:6][N:5]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>O1CCCC1>[Cl:3][C:4]1[C:9]([N:10]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 836063HCID 836063, compound

Product 1

HCID 59467510HCID 59467510, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.63 g sodium hydride (NaH) (26 mmol) and 50 mL tetrahydrofuran (THF) were added in an ice bath with stirring. 3.01 g N-(2-chloro-pyridin-3-yl)-benzamide (13 mmol) and 40 mL THF were then added and reacted for 30 min. Next, 3.28 g 1-bromo-hexane (20 mmol) was added and reacted for 24 hr. After cooling to room temperature, the reaction was quenched by water. After extraction three times by ethyl acetate, removal of water by magnesium sulphate (MgSO4), concentration, and purification by column, 2.39 g white solid was obtained, with a yield of 58%.

Workup

  1. customreacted for 30 min
  2. customreacted for 24 hr
  3. customthe reaction was quenched by water
  4. extractionAfter extraction three times
  5. customby ethyl acetate, removal of water
  6. concentrationby magnesium sulphate (MgSO4), concentration, and purification by column

Sources & evidence

ORD record
ord-c9120b3d46c447e6942f84155d4127c9
Source dataset
uspto-grants-2010_09
Patent number
US07799918B2

Reaction notes

Loading…