Indole → 3-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)-1H-indole hydroiodide

HRID 1075786Notes

Reaction equation

HRID 1075786 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:10]1[CH2:14][CH2:13][NH:12][C:11]1=[S:15].[I:16]I.[I-].[K+]>CO.O>[IH:16].[NH:12]1[CH2:13][CH2:14][N:10]=[C:11]1[S:15][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 807IodineHCID 4875Potassium IodideHCID 2723650Ethylenethiourea

Product 1

HCID 867333733-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)-1H-indole hydroiodide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 11.7 g indole in 100 ml methanol and 10.2 g 2-imidazolidinethione in 150 ml methanol is added to a well-stirred solution of 25.4 g iodine and 50 g potassium iodide in 100 ml water. The mixture is stirred for 2 hours at room temperature. The clear solution is concentrated in vacuo to one third of the original volume and cooled. The solid which separates is filtered off, dried and recrystallised from alcohol-ether to give 3-(2-imidazolin-2-ylthio)-indole hydriodide of the formula ##SPC9##

Workup

  1. concentrationThe clear solution is concentrated in vacuo to one third of the original volume
  2. temperaturecooled
  3. filtrationThe solid which separates is filtered off
  4. customdried
  5. customrecrystallised from alcohol-ether

Sources & evidence

ORD record
ord-916e7c9e10e5428fbf74d51277c5e34f
Source dataset
uspto-grants-1976_05
Patent number
US03954757

Reaction notes

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