Thionyl Chloride → 1-(6-Chlorohexyl)-3-methyl-2-(1-imidazolyl)indole

HRID 1719400Notes

Reaction equation

HRID 1719400 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH3:21])=[C:13]1[N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)(O)[O-].[Na+]>>[Cl:3][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH3:21])=[C:13]1[N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 202681751-(6-Hydroxyhexyl)-3-methyl-2-(1-imidazolyl)indole

Product 1

HCID 202681921-(6-Chlorohexyl)-3-methyl-2-(1-imidazolyl)indole

Procedure

Thionyl chloride (0.36 ml) is combined with 1-(6-hydroxyhexyl)-3-methyl-2-(1-imidazolyl)indole (1.3 g) at 0°. The mixture is then stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate is added and the mixture is extracted with dichloromethane. The extract is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Concentration to dryness and purification by chromatography gives 1-(6-chlorohexyl)-3-methyl-2-(1-imidazolyl)indole.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe extract is washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration
  5. customto dryness and purification by chromatography

Sources & evidence

ORD record
ord-322df61102c04e409372e62941e69904
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

Loading…