Indole → 1-(4-Chlorobenzyl)-1h-indole

HRID 1271069Notes

Reaction equation

HRID 1271069 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.O>CS(C)=O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydride

Product 1

HCID 9671631-(4-Chlorobenzyl)-1h-indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 5.86 g (0.05 mol) of indole in 25 ml of DMSO is added to a mixture of 1.32 g of sodium hydride (0.055 mol, mineral oil suspension) in 50 ml of dimethyl sulfoxide. The resultant mixture is heated at 60° C. for 1.3 hours; after that, it is allowed to cool down and 17.7 g (0.11 mol) of 4-chlorobenzyl chloride are added dropwise. The solution is heated to 60° C. and allowed to stand overnight; it is then poured into 200 ml of water while stirring. This mixture is extracted several times with a total of 75 ml of CH2Cl2, after which the organic phase is dried with anhydrous sodium sulfate and filtered and the filtrate is evaporated in vacuo.

Workup

  1. temperatureto cool down
  2. extractionThis mixture is extracted several times with a total of 75 ml of CH2Cl2
  3. dry with materialafter which the organic phase is dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-7149fe3b953d4abcbf7377caad674648
Source dataset
uspto-grants-2007_04
Patent number
US07205299B2

Reaction notes

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