Thionyl Chloride → HCID 54308134, compound

HRID 66909Notes

Reaction equation

HRID 66909 reaction equation
Cl.[CH3:2][C:3]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH3:20])[C:13]([CH3:21])=[C:12]2[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:7])[C:4]([OH:6])=O.S(Cl)(Cl)=O>>[CH2:13]([NH:14][C:4](=[O:6])[C:3]([CH3:2])([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH3:20])[C:13]([CH3:21])=[C:12]2[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH3:7])[CH2:12][CH3:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 3059433Propanoic acid, 2-methyl-2-((2-methyl-1-propyl-3-(4-pyridinyl)-1H-indol-5-yl)oxy)-, hydrochloride

Product 1

HCID 54308134HCID 54308134, compound

Procedure

A quantity of 0.5 g (1.3 m mole) of 2-methyl-2-[2-methyl-1-propyl-3-(4-pyridyl)-1H-indole-5-yloxy]propanoic acid hydrochloride was warmed for 15 minutes with 4 ml of thionylchloride on a steam bath. Subsequently, the excess thionylchloride was removed in vacuo, and the residue was dissolved in 100 ml of chloroform and 4 ml of propylamine were added dropwise under stirring. After one hour the reaction mixture was evaporated, and the residue obtained was purified on silicagel with ethyl acetate as eluant.

Workup

  1. customSubsequently, the excess thionylchloride was removed in vacuo
  2. dissolutionthe residue was dissolved in 100 ml of chloroform
  3. addition4 ml of propylamine were added dropwise
  4. customAfter one hour the reaction mixture was evaporated
  5. customthe residue obtained
  6. customwas purified on silicagel with ethyl acetate as eluant

Sources & evidence

ORD record
ord-b3f9df1e55b242baaa67f4609af8e7f5
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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