Thionyl Chloride → HCID 13362116, compound

HRID 1633152Notes

Reaction equation

HRID 1633152 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[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=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[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 20441678HCID 20441678, compound

Product 1

HCID 13362116HCID 13362116, compound

Procedure

Thionyl chloride (0.36 ml) is combined with 1-(6-hydroxyhexyl)-3-methyl-2-(3-pyridyl)indole (1.37 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 brine and dried over anhydrous magnesium sulfate. Concentration in vacuo yields the crude chloride as an oil. Purification by silica gel chromatography (CH2Cl2 /EtOAc 9.5:0.5) gives 1-(6-chlorohexyl)-3-methyl-2-(3-pyridyl)indole as a light yellow oil; NMR (CDCl3) δ3.30 (t, 2H), 3.92 (t, 2H).

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe extract is washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration in vacuo
  5. customyields the crude chloride as an oil
  6. customPurification by silica gel chromatography (CH2Cl2 /EtOAc 9.5:0.5)

Sources & evidence

ORD record
ord-c27dde6537e54d44af9d1aca36896efa
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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