Potassium Hydroxide → HCID 11482194, compound

HRID 890239Notes

Reaction equation

HRID 890239 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[CH:7]2.[OH-].[K+].Br[CH2:15][CH2:16][CH2:17][S:18][CH3:19]>COCCOCCN(CCOCCOC)CCOCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:15][CH2:16][CH2:17][S:18][CH3:19])[C:8]([CH3:11])=[CH:7]2

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 1144656368731-27-13×HCID 118160627-chloro-2-methyl-1H-indole

Product 1

HCID 11482194HCID 11482194, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-Catalyst2×

Procedure

1.5 g of 7-chloro-2-methyl-1H-indole are mixed with stirring with 1.1 g of ground potassium hydroxide and 0.2 g of TDA-1. The mixture is left stirring for 2 hours at AT, then 3.1 g of 1-bromo-3-methylsulphanylpropane are added dropwise and the mixture is heated at reflux for 24 hours. Ground potassium hydroxide (0.5 g), TDA-1 (0.1 g) and 1.6 g of 1-bromo-3-methylsulphanylpropane are again added. After heating at reflux for 9 hours, 1.6 g of 1-bromo-3-methylsulphanylpropane are again added and the mixture is heated at reflux for 24 hours. The mixture is allowed to return to AT and is then extracted with toluene. The organic phase is washed with a 10% HCl solution, with water and then a saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica while eluting with a cyclohexane/toluene (50/50, v/v) mixture. 1.87 g of the expected compound are obtained.

Workup

  1. waitThe mixture is left
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 24 hours
  4. temperatureAfter heating
  5. temperatureat reflux for 9 hours
  6. temperaturethe mixture is heated
  7. temperatureat reflux for 24 hours
  8. extractionis then extracted with toluene
  9. washThe organic phase is washed with a 10% HCl solution, with water
  10. customIt is dried
  11. customevaporated
  12. customthe residue is chromatographed on silica
  13. washwhile eluting with a cyclohexane/toluene (50/50

Sources & evidence

ORD record
ord-c0304803a7114e1bbe60a7f011a9c45a
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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