Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 18469781, compound

HRID 2228372Notes

Reaction equation

HRID 2228372 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)([O-:5])=[O:4].[Cl:15][CH2:16][CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[Cl:15][CH2:16][CH2:17][N:10]1[C:11]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indole

Product 1

HCID 18469781HCID 18469781, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a flask of 500 ml capacity fitted with a stirrer and cooling tube, there were introduced 7.2 g (corresponding to 0.21 mol) of an NaH oil dispersion, and 50 ml of tetrahydrofuran. The mixture was stirred on an ice-water bath. To this mixture was added, dropwise, little by little, a solution of 34.02 g of 4-nitroindole (0.21 mol) dissolved in 100 ml of tetrahydrofuran. After completion of the dropwise addition, the ice-water bath was removed and the mixture was stirred for one hour at room temperature. Then, 49.29 g (0.21 mol) of 2-chloroethyl-p-toluenesulfonate were added, and was reacted for 10 hours while stirring, heating under reflux. After completion of the reaction, the insoluble material was removed by filtration, and concentration was performed under reduced pressure. Further, this reaction mixture was purified by column chromatography using silica gel, to obtain 14.9 g of 1-(2-chloroethyl)-4-nitroindole.

Workup

  1. customInto a flask of 500 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. additionTo this mixture was added
  4. additionAfter completion of the dropwise addition
  5. customthe ice-water bath was removed
  6. stirringthe mixture was stirred for one hour at room temperature
  7. customwas reacted for 10 hours
  8. stirringwhile stirring
  9. temperatureheating
  10. temperatureunder reflux
  11. customAfter completion of the reaction
  12. customthe insoluble material was removed by filtration, and concentration
  13. customFurther, this reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-2cf1e7fd7d7943ed9d387f13197e5883
Source dataset
uspto-grants-2002_07
Patent number
US06416939B1

Reaction notes

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