1-Bromo-3-chloropropane → HCID 14201489, compound

HRID 2296735Notes

Reaction equation

HRID 2296735 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:4][C:3]=1[CH3:18].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][Cl:25]>CN(C)C=O>[Cl:25][CH2:24][CH2:23][CH2:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 18388179HCID 18388179, compound

Product 1

HCID 14201489HCID 14201489, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The product of Step B (6.0 g) in N, N-dimethylformamide (200 mL) was added to a suspension of 60% sodium hydride (2.0 g) in N, N-dimethylformamide (200 mL). The mixture was stirred at ambient temperature for 1 hour and then treated with 1-bromo-3-chloropropane (30 mL). The mixture was stirred at ambient temperature for 18 hours and partitioned between ethyl acetate and water. The organic portion was washed with water, dried over sodium sulfate, filtered and evaporated to give the title compound (6.2 g).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 18 hours
  2. custompartitioned between ethyl acetate and water
  3. washThe organic portion was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7a704b8d6196457f807c07864fdbe92c
Source dataset
uspto-grants-2002_12
Patent number
US06489337B1

Reaction notes

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