1-Bromo-3-chloropropane → HCID 12798089, compound

HRID 647517Notes

Reaction equation

HRID 647517 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CN(C)C=O>[Cl:24][CH2:23][CH2:22][CH2:21][N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH:12]=[N:13]1.[Cl:24][CH2:23][CH2:22][CH2:21][N:13]1[CH:12]=[C:11]2[C:15]([CH:16]=[CH:17][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10]2)=[N:14]1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 127980885-(Benzyloxy)-1H-indazole

Product 2

HCID 12798089HCID 12798089, compoundHCID 12798090HCID 12798090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-benzyloxyindazole (30 g) in dimethylformamide (150 ml), 50% sodium hydride (6.7 g) was added and the mixture was stirred at room temperature for 10 minutes. The solution was then added dropwise to 150 ml of dimethylformamide containing 1-bromo-3-chloropropane (30 g) while cooling with ice, and, after stirring at room temperature for 30 minutes, the mixture was extracted with benzene. The extract was washed with water, dried over anhydrous sodium sulfate, and distilled to remove the solvent used. The residue was chromatographed with a column filled with silica gel to give 16 g of 1-(3'-chloropropyl)-5-benzyloxyindazole (m. p. 65°-66° C.) and 4.5 g of 2-(3'-chloropropyl)-5-benzyloxyindazole (m.p. 97°-98° C.).

Workup

  1. temperaturewhile cooling with ice
  2. stirringafter stirring at room temperature for 30 minutes
  3. extractionthe mixture was extracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue was chromatographed with a column
  9. additionfilled with silica gel

Sources & evidence

ORD record
ord-09e848e5da1941838c965a9a418417e7
Source dataset
uspto-grants-1983_10
Patent number
US04409234

Reaction notes

Loading…