1-Bromo-3-chloropropane → HCID 21884285, compound

HRID 890246Notes

Reaction equation

HRID 890246 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:12]([Cl:13])=[C:11]2[C:7]([CH:8]=[C:9]([CH3:14])[NH:10]2)=[CH:6][CH:5]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:3][C:4]1[C:12]([Cl:13])=[C:11]2[C:7]([CH:8]=[C:9]([CH3:14])[N:10]2[CH2:16][CH2:17][CH2:18][Cl:19])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 12096330HCID 12096330, compound

Product 1

HCID 21884285HCID 21884285, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

7.84 g of crushed sodium hydroxide, 190 ml of toluene, 7 g of 6,7-dichloro-2-methyl-1H-indole, 85 ml of toluene and 0.7 g of tetrabutylammonium hydrogensulphate are introduced under nitrogen. The mixture is heated at reflux for 30 minutes, then 14 ml of 1-bromo-3-chloropropane are added and reflux is maintained for 2 hours. The reaction medium is poured onto water and the aqueous phase is washed with toluene. Extraction is carried out with toluene and then the extract is washed with water and with a saturated NaCl solution. The extract is dried and evaporated to produce 11.3 g of the expected compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 30 minutes
  3. temperaturereflux
  4. temperatureis maintained for 2 hours
  5. additionThe reaction medium is poured onto water
  6. washthe aqueous phase is washed with toluene
  7. extractionExtraction
  8. washthe extract is washed with water and with a saturated NaCl solution
  9. customThe extract is dried
  10. customevaporated

Sources & evidence

ORD record
ord-3d8da33dd4a445999b1e4a6b1fd4846c
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

Loading…